Herbicidal sulfonylureas

ABSTRACT

The invention relates to herbicidal sulfonylurea compounds, agriculturally suitable compositions thereof and a method for their use as general or selective preemergent or postemergent herbicides or plant growth regulants.

CROSS-REFERENCE TO RELATED APPLICATION

This is a continuation-in-part of U.S. Ser. No. 07/468,283 filed Jan.22, 1990.

BACKGROUND OF THE INVENTION

This invention relates to certain herbicidal sulfonylureas,agriculturally suitable compositions thereof and a method for their useas general or selective preemergent or postemergent herbicides or asplant growth regulants.

New compounds effective for controlling the growth of undesiredvegetation are in constant demand. In the most common situation, suchcompounds are sought to selectively control the growth of weeds inuseful crops such as cotton, rice, corn, wheat and soybeans, to name afew. Unchecked weed growth in such crops can cause significant losses,reducing profit to the farmer and increasing costs to the consumer. Inother situations, herbicides are desired which will control all plantgrowth. Examples of areas in which complete control of all vegetation isdesired are areas around railroad tracks, storage tanks and industrialstorage areas. There are many products commercially available for thesepurposes, but the search continues for products which are moreeffective, less costly and environmentally safe.

EP-A-238,070 discloses herbicidal sulfonylureas of the general formula##STR1## wherein: Q is a condensed heterocyclic group having an N atomin the bridgehead, which may be substituted.

SUMMARY OF THE INVENTION

Now new compounds have been found that are preemergence and/orpostemergence herbicides or plant growth regulants. Accordingly, thecompounds of the invention are compounds of the formula ##STR2##wherein: L is ##STR3## Q is O, S or NR⁸ ; Q¹ is O or NR⁸ ;

Q² is O, S or NCH₃ ;

R is H or CH₃ ;

R¹ is H, CH₃, Cl or Br;

R² is H or CH₃ ;

R³ is H, CH₃, F, Cl or Br;

R⁴ is H, CH₃, F, Cl or Br;

R⁵ is H or C₁ -C₃ alkyl;

R⁶ is H, C₁ -C₃ alkyl, C₁ -C₃ alkoxy, F, Cl, (C₁ -C₂ alkyl)carbonyloxyor C₁ -C₂ alkylsulfonyloxy;

R⁷ is CO₂ R⁹, CO₂ NR¹⁰ R¹¹, S(O)₂ NR¹⁰ R¹¹ or S(O)₂ R¹² ;

R⁸ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, allyl, propargyl or C₂ -C₄alkoxyalkyl;

R⁹ is C₁ -C₄ alkyl;

R¹⁰ is H or C₁ -C₂ alkyl;

R¹¹ is H or C₁ -C₂ alkyl;

R¹² is C₁ -C₃ alkyl;

W is CR¹³ or N;

R¹³ is H, CH₃, Cl or Br;

m is 0, 1 or 2;

n is 0 or 1; ##STR4## X is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylthio,halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃alkylamino or di(C₁ -C₃ alkyl)amino;

Y is H, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅alkoxyalkoxy, amino, C₁ -C₃ alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄alkenyloxy, C₃ -C₄ alkynyloxy, C₂ -C₅ alkylthioalkyl, C₂ -C₅alkylsulfinylalkyl, C₂ -C₅ alkylsulfonylalkyl, C₁ -C₄ haloalkyl, C₂ -C₄alkynyl, C₃ -C₅ cycloalkyl, azido, cyano, ##STR5## or N(OCH₃)CH₃ ; p is2 or 3;

Q³ and Q⁴ are independently O or S;

R¹⁴ is H or C₁ -C₃ alkyl;

R¹⁵ and R¹⁶ are independently C₁ -C₃ alkyl;

Z is CH, N, CCH₃, CC₂ H₅, CCl or CBr;

Z¹ is CH or N;

Y¹ is O or CH₂ ;

X¹ is CH₃, OCH₃, OCH₂ CH₃ or OCF₂ H;

X² is CH₃, CH₂ CH₃ or CH₂ CF₃ ;

Y² is OCH₃, OCH₂ CH₃, SCH₃, SCH₂ CH₃, CH₃ or CH₂ CH₃ ;

X³ is CH₃ or OCH₃ ;

Y³ is H or CH₃ ;

X⁴ is CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃ or Cl; and

Y⁴ is CH₃, OCH₃, OCH₂ CH₃ or Cl;

and their agriculturally suitable salts;

provided that

1) when X is halogen, then Z is CH and Y is OCH₃, OCH₂ CH₃, NH₂, NHCH₃,N(CH₃)₂, OCF₂ H, OCF₂ Br or N(OCH₃)CH₃ ;

2) when X or Y is C₁ haloalkoxy, then Z is CH; and

3) X⁴ and Y⁴ are not simultaneously Cl.

In the above definitions, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl", denotes straightchain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or thedifferent butyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propyloxy, isopropyloxy and thedifferent butyloxy isomers.

Alkenyl denotes straight chain or branched alkenes, e.g. 1-propenyl,2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g. ethynyl,1-propynyl, 2-propynyl and the different butynyl isomers.

Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the differentpropylsulfonyl isomers.

Alkylthio, alkylsulfinyl, alkylamino, etc. are defined analogously tothe above examples.

Cycloalkyl denotes cyclopropyl, cyclobutyl and cyclopentyl.

The term "halogen", either alone or in compound words such as"haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as "haloalkyl" said alkyl may bepartially halogenated or fully substituted with halogen atoms and saidhalogen atoms may be the same or different. Examples of haloalkylinclude CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 5. Forexample, C₁ -C₃ alkylsulfonyl would designate methylsulfonyl throughpropylsulfonyl and C₂ alkoxyalkoxy would designate OCH₂ OCH₃.

Compounds of the invention preferred for reasons of increased ease ofsynthesis and/or greater herbicidal efficacy are:

1. Compounds of Formula I where

A is A-1

X is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F, Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl or CH₂ Br;

Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃, NHCH₃,N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CH₂OCH₃, CH₂ SCH₃, ##STR6##

OCF₂ H, SCF₂ H, cyclopropyl, C.tbd.CH or C.tbd.CCH₃ ;

R¹⁴ is H or CH₃ ;

R¹⁵ and R¹⁶ are independently CH₃ or CH₂ CH₃ ;

Z is CH or N; and

R is H.

2. Compounds of Preferred 1 wherein L is L-1, L-2, L-3, L-7, L-8 or L-9.

3. Compounds of Preferred 2 where R⁸ is H, C₁ -C₃ alkyl or allyl.

4. Compounds of Preferred 3 where

Z is CH;

X is CH₃, OCH₃, OCH₂ CH₃, Cl or OCF₂ H; and

Y is CH₃, OCH₃, CH(OCH₃)₂ or OCF₂ H.

5. Compounds of Preferred 4 where

L is L-1; and

W is CH.

6. Compounds of Preferred 4 where

L is L-2.

7. Compounds of Preferred 4 where

L is L-7.

Compounds of the invention specifically preferred for reasons ofgreatest ease of synthesis and/or greatest herbicidal efficacy are:

3,4-dihydro-N-[[(4-methoxy-6-methyl-2-pyrimidin-2-yl)amino]carbonyl]-1-oxo-1H-[1,4]-oxazine[4,3-a]indole-10-sulfonamide;

3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-1-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide;

N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-4-dihydro-2H-pyrrolo[1,2-e][1,2,5]thiadiazine-8-sulfonamide,1,1-dioxide;

N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3,4-dihydro-2-methyl-2H-pyrazolo[1,5-e][1,2,5]thiadiazine-8-sulfonamide,1,1-dioxide.

This invention also comprises novel compounds, such as thepyrrolesulfonamides of Formulas II and III, useful as intermediates tothe compounds of Formula I. ##STR7## wherein R¹⁷ is H or C(CH₃)₃ ; andLSO₂ NH₂ III

wherein

L is as defined above.

The compounds of this invention are active preemergent and postemergentherbicides and plant growth regulants. Some are especially useful forselective control of grass weeds in broad leaf crops such as cotton andsoybeans.

DETAILED DESCRIPTION OF THE INVENTION SYNTHESIS Compounds of theInvention

The sulfonylureas of Formula I may be prepared by a number of methods.These methods are described below, along with the appropriate referencesfor greater detail. ##STR8##

One method of synthesis of sulfonylureas of Formula I is depicted inEquation 1 wherein R, A, and L are as defined above. Asulfonylisocyanate of Formula 3 is contacted with a heterocyclic amineof Formula 2 in an inert solvent to afford sulfonylurea of Formula I.Reaction time necessary can vary from several minutes to 24 hours ormore, and temperature is preferably in the range of 20° to 80° C. Usefulsolvents for this reaction include aprotic inert solvents such asacetonitrile, dichloromethane, etc.

U.S. Pat. Nos. 4,127,405, 4,257,802 and 4,221,585 disclose this equationand are herein incorporated by reference. ##STR9##

Another method of synthesis of compounds of Formula I is depicted inEquation 2 wherein A, R, and L are as defined previously and R¹⁸ islower alkyl such as methyl or ethyl and so on. In this reaction, asulfonamide of Formula 4 is contacted with an alkyl carbamate of Formula5 in the presence of a trialkylaluminum in an inert solvent such asdichloromethane, 1,2-dichloroethane, etc., and subsequently treated withaqueous acid to afford sulfonylureas of Formula I. This reaction istaught in EP-A-83,975 (published Jul. 20, 1983). ##STR10##

A third method of preparation for herbicides of Formula I is depicted inEquation 3 wherein A, R, and L are as defined previously, and Arrepresents an aryl group, for example a phenyl or substituted phenylgroup. In this reaction, a sulfonamide of Formula 4 is contacted with anaryl carbamate of Formula 6 and a base such as1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in an inert solvent such asacetonitrile or p-dioxane, and subsequently treated with aqueous acid toafford sulfonylureas of Formula I. The reaction is taught inEP-A-44,807, and EP-A-85,028.

Compounds of Formula I are generally best prepared by the procedureoutlined in Equation 3. The methods of Equations 1 and 2 may, in manycases, be equally well employed to prepare compounds of Formula I.

Intermediate Compounds

Heterocyclic sulfonyl isocyanates of Formula 3 may be prepared byprocedures taught in U.S. Pat. No. 4,127,405.

Heterocyclic carbamates of Formula 5 are prepared by procedures taughtin EP-A-83,975. The heterocyclic carbamates of Formula 6 may be preparedby procedures taught in EP-A-44,807, EP-A-72,347, EP-A-173,498, U.S.Pat. No. 4,666,506, and references cited therein.

The sulfonamides 4 of this invention may be prepared in a variety ofways, some of which are described in Equations 4 through 13 and Equation15.

Precursors to sulfonamides of Formula 4 where L contains a pyrrole orpyrazole ring (L-1, L-3, L-5, L-7, L-9, L-11, L-13, L-15, L-18) aredepicted in Formula 7. The bicyclic fused ring sulfonamides of Formula 4may be synthesized from these precursors, where R¹⁹ is a suitableprotecting group such as tert-alkyl or trialkylsilyl, by a variety ofmethods, some of which are described in Equations 4 through 13.##STR11##

Similarly, precursors to sulfonamides of Formula 4 where L contains anindole ring system (L-2, L-4, L-6, L-8, L-10, L-12, L-14, L-16, L-19)are indole-3-sulfonamides of Formula 8, where R¹⁹ is a suitableprotecting group as defined above. ##STR12##

The methods that will be described for the conversion of sulfonamides ofFormula 7 to bicyclic sulfonamides of Formula 4 are equally applicablefor the conversion of indole-3-sulfonamides 8 to tricyclic sulfonamidesof Formula 4; therefore, only the transformations of 7 will be outlinedbelow.

Sulfonamides of Formula 4 where L is L-1 and R¹⁹, R² and Q are aspreviously defined, X⁵ is a suitable leaving group such as chloro,bromo, iodo, alkyl- or arylsulfonate, and R²⁰ is a suitable protectinggroup such as trialkylsilyl, tetrahydropyran-2-yl, may be prepared asoutlined in Equation 6. ##STR13##

Sulfonamide 7 is treated with a base such as an alkali metal alkoxide,hydride or tertiary amine and an appropriate electrophilic reagent asshown in an inert solvent, preferably a polar aprotic solvent such asdimethylformamide (DMF) to afford intermediate 9. In the case where Q isoxygen, the electrophilic reagent may also be ethylene oxide orpropylene oxide to afford sulfonamides 9 where QR²⁰ is OH. Sulfonamide 9is then metalated on carbon using an excess of organometallic base,preferably an organolithium reagent such as n-butyllithium in an inertsolvent such as diethyl ether or tetrahydrofuran (THF), under anhydrousconditions, followed by quenching with carbon dioxide to affordsulfonamides 10. The protecting groups R²⁰ are then removed byappropriate methods known to one skilled in the art. The resultantsulfonamides are then cyclized under dehydrating conditions, for exampleby heating in an aprotic solvent with acid catalysis and removal ofwater by azeotropic distillation.

Sulfonamides of Formula 4 where L is L-3 or L-9 may be prepared fromcorresponding sulfonamides of Formula 4 where L is L-1 or L-7 by knownmethods of dehydrogenation such as heating in a suitable inert solventwith dehydrogenating agents such as palladium on carbon or manganesedioxide. Additionally, sulfonamides of Formula 4 where L is L-3 and Q isO or S may be prepared from the corresponding acetals or ketals 12 asdepicted in Equation 7, wherein R¹, R¹⁹, and X⁵ are as definedpreviously and R²¹ is lower alkyl or the two QR²¹ groups may be takentogether to form a cyclic ketal such as 1,3-dioxolane or 1,3-dioxanering. ##STR14## Subsequent metalation, quenching with carbon dioxide,and acid catalyzed cyclization as described above for Equation 6, affordsulfonamides of Formula 4 where L is L-3.

Preparation of sulfonamides 4 where L is L-5 may be accomplished by asimilar sequence of reactions to that of Equation 6 and is outlined inEquation 8, wherein X⁵, R¹⁹, R²¹, n and R¹ are as previously defined, R³and R⁴ are H, F, or CH₃, and Q⁵ is O or NCH₃. ##STR15## Sulfonamide 7 istreated with base as described above and a suitable electrophilicreagent to afford the carboxylic acid derivative 13. Metalation with asuitable base taken in at least two-fold excess relative to 13 resultsin cyclization to 14 after aqueous work-up. Protecting group removalaffords sulfonamides of Formula 15. Sulfonamides 15 where R³ and/or R⁴is chloro or bromo may be prepared from the corresponding ketones 15where R³ and/or R⁴ is hydrogen by standard halogenation reactions knownto one skilled in the art.

Unsaturated ketone sulfonamides 4 where L is L-18 or L-19 can beprepared from the corresponding saturated ketone sulfonamideintermediates 4 where L is L-5 or L-6 respectively using a variety ofstandard oxidation methods known in the literature; for example, by thechlorination, dehydrochlorination sequence described in "OrganicSyntheses" Coll. Vol. IV, p. 162 (1963, John Wiley).

Sulfonamides of Formula 4 where L is L-7 may be prepared as outlined inEquation 9, wherein R¹, R², R¹⁹ and Q¹ are as previously defined, andR²² is a trialkylsilyl protecting group. ##STR16## Metalation ofsulfonamide 9 as described earlier in Equation 6, followed by quenchingwith sulfur dioxide affords sulfinic acid derivative 16. Thisintermediate may then be oxidized to sulfonyl chloride 17 using any of avariety of chlorinating reagents such as N-chlorosuccinimide, sodiumhypochlorite, chlorine and the like. Protecting group removal inducescyclization to sulfonamides 18.

Preparation of sulfonamides 4 where L is L-11 may be achieved throughthe sequence outlined in Equation 10, wherein R¹, R¹⁹, X⁵ and W are aspreviously defined. ##STR17## Sulfonamide of Formula 7 may be alkylatedon nitrogen with a suitable electrophilic reagent containing a disulfideusing conditions described in Equation 6 to afford intermediates 19.Metalation of 19 results in cyclization to cyclic sulfide 20 which canthen be further oxidized with a suitable oxidant such as a peroxy acidor hydrogen peroxide to sulfoxides (m=1) or sulfones (m=2). Sulfonamideprotecting group removal affords bicyclic sulfonamides 21.

The preparation of sulfonamides of Formula 4 wherein L is L-13 isdepicted in Equation 11, wherein R¹, R⁵, R¹⁹, R²⁰, Q², and W are aspreviously defined. ##STR18##

Metalation of 9 as described above, followed by quenching with analdehyde, R⁵ CHO, affords alcohols 22. This alcohol is converted to aleaving group, X⁵, such as halogen, or sulfonate, using standardmethods. Removal of protecting group R²⁰, followed by treatment withbase, as needed, induces cyclization to sulfonamides 24.

Sulfonamides of Formula 4 where L is L-15 may be prepared as outlined inEquation 12, wherein R¹⁹ is tert-alkyl, R⁶ is H or alkyl, and R²² is atrialkylsilyl protecting group. ##STR19## Silyl protecting group R²² maybe removed from 25 using fluoride in some form, then the resultingalcohol is converted to a suitable leaving group X⁵, described above.Metalation of intermediate 26 affords bicyclic sulfonamide 27.

Alternatively, for sulfonamides of Formula 4 where L is L-15, and R⁶ isas described in the Summary, the methods depicted in Equation 13 may beused. ##STR20##

The ketone 14, wherein R³ ═R⁴ ═H, described in Equation 8 can be furthertreated with reducing agents such as borohydrides, aluminum hydrides andthe like to afford the corresponding alcohols 28. Conversion of thisalcohol to a variety of derivatives such as halides, ethers, esters,sulfonates as encompassed by R⁶ may then be achieved by standard methodswidely known in the art.

Pyrrole-3-sulfonamide precursors 7 wherein W═CH, R¹ ═H and R¹⁹ is asuitable protecting group as defined above are available from thecorresponding bromo pyrrole 30 as depicted in Equation 14, wherein R²³is lower alkyl, such as isopropyl. ##STR21##

N-silyl-protected pyrrole 30, where R²³ is preferably an isopropylgroup, is treated with an alkyllithium reagent such as n-butyllithium asdescribed in Chem. Ber., Vol. 122, p. 169 (1989), and references citedtherein. The resultant metalated species is treated with sulfur dioxideto afford sulfinate salt 31 which is then converted to sulfonamide 32 byany of a number of known methods, for example, treatment withN-chlorosuccinimide followed by amination with an appropriate primaryamine as disclosed in U.S. Pat. No. 4,481,029. The N-silyl group is thenremoved, most conveniently with an alkali fluoride or quaternaryammonium fluoride salt, to afford pyrrole-3-sulfonamide 33 (equivalentto Formula 7 wherein R¹ ═H, W═CH). Additional derivatives of Formula 7where R¹ is other than H, and W is CR¹³ (where R¹³ ≠H) may be preparedby analogous methods. In sulfonamides of Formula 4 in the pyrrole andpyrazole series, where R¹ and/or R² is chloro or bromo, it may be morepractical to introduce the halogens via a halogenation reaction on thecorresponding unsubstituted bicyclic sulfonamides.

Pyrrole-2-sulfonamides where L is L-17 are available from precursors 35as depicted in Equation 15, wherein R¹⁹, R²⁰, R²³, X⁵, and R⁷ are asdefined above, and R⁹ is t-butyl. ##STR22##

Pyrrole derivatives 35 are available from the 3-bromo derivative 30 asdescribed in Equation 14, using the appropriate electrophilic reagent inplace of sulfur dioxide that would be apparent to one skilled in theart. N-Alkylation followed by metalation, sulfur dioxide treatment, andconversion of the sulfinate to a sulfonamide 37 proceeds by methodsdescribed above, for example, in Equations 6 and 9. Subsequentconversion of 37 to 38 where X⁵ is a leaving group such as a sulfonateester, followed by metalation analogous to that described in Equation12, affords the bicyclic pyrrole-2-sulfonamides 39.

In the case where R⁷ is an ester functionality, esters in which R⁹ isother than t-butyl may be prepared from the t-butyl ester by heating 39in the appropriate alcohol solvent with acid catalysis to effect atransesterification to sulfonamides 39 wherein R⁹ is C₁ -C₄ alkyl.

Indole-3-sulfonamide precursors 40 are available via the sequenceoutlined in Equation 16, wherein R¹ and R¹⁹ are as previously defined,and X⁶ is chloro or bromo. ##STR23##

O-Nitro toluenes 41 are converted to benzylic halides 42 withhalogenating agents such as N-bromosuccinimide, and subsequently tosulfonamides 45 by known methods, for example, as reported in U.S. Pat.No. 4,420,325. The nitro group of 45 is reduced to aniline 46 with anyof a number of reducing agents such as iron powder in acetic acid,hydrogen and palladium metal catalyst, and the like. Formylation to 47occurs upon reaction with formic acetic anhydride, then dehydration toisonitrile 48 is achieved with a variety of reagents, for example, withdiphosgene and base as described in Chem. Ber., Vol. 121, p. 507 (1988),J. Org. Chem., Vol. 45, p. 4059 (1980), and Angewandte Chem. Int'l. Ed.,Vol. 16, p. 259 (1977). Cyclization of 48 to 40 occurs upon addition ofa strong base such as lithium dialkylamide bases, preferably withcooling of the reaction medium below ambient temperature, followed bywork-up with aqueous acid.

Pyrazole sulfonamide intermediates 49 are known to be available from thecorresponding pyrazoles as depicted in Equation 17 and taught in U.S.Pat. No. 3,665,009. ##STR24## Metalation of 49 and subsequent reactionwith electrophiles as depicted in Equations 6 through 12 is furtherdescribed in EP-A-95,925 (published Dec. 7, 1983).

The heterocyclic amines of Formula (2a) to (2g) below are either known,or can be prepared by obvious methods by one skilled in the art.##STR25##

For a review of the synthesis and reactions of 2-amino- and2-methylaminopyrimidines see The Chemistry of Heterocyclic Compounds,Vol. 16, Wiley-Interscience, New York (1962). For a review of thesynthesis and reactions of 2-amino- and 2-methylamino-s-triazines, seeThe Chemistry of Heterocyclic Compounds, Vol. 13, Wiley-Interscience,New York (1959), F. C. Schaefer, U.S. Pat. No. 3,154,537 and F. C.Schaefer and K. R. Huffman J. Org. Chem., 28, 1812 (1963). J. Chem.Soc., 2031 (1986), EP-A-173,498 and U.S. Pat. No. 4,666,506 describefurther methods. The synthesis of the bicyclic amines (2b) and (2c) istaught in U.S. Pat. No. 4,339,267. The synthesis of bicyclic amines (2d)is taught in European Patent Application EP-A-46,667.

Compounds of Formula (2e) are described in EP-A-73,562. Compounds ofFormula (2f) are described in EP-A-94,260.

The amines of Formula (2q) can be prepared by methods taught inEP-A-125,864 (published Nov. 11, 1984) or by suitable modifications thatwould be obvious to one skilled in the art.

The amines of Formula (2) where X or X¹ is OCF₂ H and/or Y is OCF₂ H orSCF₂ H can be prepared by methods taught in EP-A-72,347, or by suitablemodifications that would be obvious to one skilled in the art.

The pyrimidines of Formula (2a) (Z=CH) where Y is ##STR26## preparedaccording to the methods taught in European Patent Applicant EP-A-84,224or suitable modifications thereof known to one skilled in the art.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by direct contactof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali or quaternary amine salt) with a solution containing the cationto be exchanged. This method is most effective when the desired saltcontaining the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble, e.g., a potassium, sodium orcalcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is furtherillustrated by the following specific examples. Temperatures arereported in degrees Celsius; abbreviations for nuclear magneticresonance (NMR) are: s=singlet, d=doublet, t=triplet, m=multiplet, andpeak positions are reported as parts per million downfield from internaltetramethylsilane. Infrared (IR) peak positions are given in reciprocalcentimeters (cm⁻¹) and sh denotes a shoulder.

EXAMPLE 1N-(1,1-Dimethylethyl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole-3-sulfonamide

A solution of 4.55 g (0.0151 mol) of 3-bromo-N-triisopropylsilylpyrrolein 100 mL anhydrous tetrahydrofuran (THF) under nitrogen atmosphere wascooled to -60° C. then treated with 10.4 mL of 1.6M butyllithium inhexanes (0.0166 mol) dropwise at such a rate as to keep the temperaturebelow -60° C. After ca. 30 minutes at this temperature, liquified sulfurdioxide was added (3.9 mL, 0.090 mol). The brown solution was thenwarmed to room temperature, and the THF was removed under reducedpressure. The resulting light brown solid was dissolved in 100 mL aceticacid and then treated with 2.0 g (0.015 mol) N-chlorosuccinimide withcooling to keep the temperature less than 25° C. After 2 hours, theacetic acid was evaporated under reduced pressure and the residue takenup in ethyl acetate. This solution was washed successively with water,NaHCO₃ solution, 5% NaHSO₃ solution, NaHCO₃ solution, brine, then driedwith MgSO₄ and evaporated in vacuo. The resulting dark brown oil residuewas dissolved in methylene chloride (200 mL) and treated with 8 mL(0.075 mol) t-butylamine and then stirred for 3 days at ambienttemperature. The solution was then washed with 1N HCl, dried (MgSO₄),and evaporated to a dark oil. Chromatography on silica gel (10% ethylacetate/hexanes) afforded 4.0 g of the title compound as an amber oilthat solidified on standing.

NMR (CDCl₃, 200 MHz) δ: 0.80 (d, 18H), 1.22 (s, 9H), 1.45 (m, 3H), 4.32(s, NH), 6.55 (m, 1H), 6.72 (m, 1H), 7.25 (m, 1H). IR (nujol): 3240cm⁻¹.

EXAMPLE 2 N-(1,1-Dimethylethyl)-1H-pyrrole-3-sulfonamide

A solution ofN-(1,1-dimethylethyl)-1-[tris(1-methylethyl)sily]-1H-pyrrole-3-sulfonamide(1.7 g, 4.7 mmol) in 25 mL THF was treated with 5.2 mL of 1Mtetrabutylammonium fluoride/THF solution, followed by 0.3 mL of aceticacid. After stirring 30 minutes at room temperature, the reactionmixture was filtered through silica with THF rinse, and the filtratestripped. The solid residue was triturated with hexanes to afford 0.77 gof tan solids, m.p. 145°-147° C. dec.

NMR (CDCl₃, 400 MHz) δ: 1.27 (s, 9H), 4.36 (s, NH), 6.52 (m, 1H), 6.80(m, 1H), 7.31 (m, 1H), 8.58 (s, NH). IR (nujol): 2270, 2360, 1300, 1125cm⁻¹.

EXAMPLE 3N-(1,1-Dimethylethyl)-1-[2-[(1,1-dimethylethyl)-dimethylsilyloxylethyl]-1H-pyrrole-3-sulfonamide

A solution of 0.99 g (4.49 mmol) ofN-(1,1-dimethylethyl)-1H-pyrrole-3-sulfonamide in 10 mLN,N-dimethylformamide (DMF) was cooled to 15° C. under nitrogenatmosphere. To this was added 1.41 g (5.9 mmol) of(2-bromoethoxy)(1,1-dimethylethyl)dimethylsilane followed by 0.61 g (5.4mmol) of potassium t-butoxide. The mixture was briefly warmed to 60° C.then cooled, diluted with diethyl ether, washed three times with 1N HCl,once with brine, dried (MgSO₄) and evaporated under reduced pressure.The resulting solids were triturated with hexanes and collected byfiltration to afford 1.31 g of the title compound, m.p. 73°-76° C.

NMR (CDCl₃, 200 MHz) δ: 0.86 (s, 9H), 1.26 (s, 9H), 3.83 (t, 2H), 3.94(t, 2H), 4.25 (s, NH), 6.40 (m, 1H), 6.65 (m, 1H), 7.17 (m, 1H). IR(nujol): 3280 cm⁻¹.

EXAMPLE 43-[[(1,1-Dimethylethyl)amino]sulfonyl]-1-[2-[(1,1-dimethylethyl)dimethylsilyloxylethyl]-1H-pyrrole-2-carboxylicacid

To a solution of 1.30 g (3.61 mmol) ofN-(1,1-dimethylethyl-1-[2-[(1,1-dimethylsilyloxy]ethyl]-1H-pyrrole-3-sulfonamidein 30 mL THF under nitrogen atmosphere cooled to -60° C. was addeddropwise 5.7 mL (9.03 mmol) 1.6M butyllithium in hexanes. The resultantyellow solution was warmed to 0° C. for 20 minutes then recooled to lessthan -60° C. and a large excess of crushed dry ice (4.5 g of CO₂) wasadded in one portion. After warming to room temperature, the mixture wasacidified with 1N HCl and water, extracted with ethyl acetate threetimes. The organic extracts were washed with brine, dried (Na₂ SO₄) andevaporated in vacuo. The residue was crystallized by dissolving theresidue in ether and adding five volumes of hexane to afford 1.17 g ofthe title compound, m.p. 107°-122° C.

NMR (CDCl₃, 200 MHz) δ: 0.82 (s, 9H), 1.25 (s, 9H), 3.88 (t, 2H), 4.45(t, 2H), 5.4 (s, NH), 6.68 (d, 1H), 6.91 (d, 1H). IR (nujol): 1670, 3300cm⁻¹.

EXAMPLE 5 3,4-Dihydro-1-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide

A mixture of 0.33 g (5.8 mmol) potassium fluoride, 1 mL water and 20 mLtrifluoroacetic acid was stirred at room temperature while 1.17 g (2.9mmol) of3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-[2-[1,1-dimethylethyl)dimethylsilyloxy]ethyl]-1H-pyrrole-2-carboxylicacid was added gradually. After several hours at room temperature, thesolvent was evaporated under reduced pressure, 15 mL water was added,and the product extracted with five 50 mL portions of ethyl acetate. Theorganic extract was dried (MgSO₄) and stripped to 0.67 g of3-(aminosulfonyl)-1-(2-hydroxyethyl)-1H-pyrrole-2-carboxylic acid. Thisresidue was taken up in 5 mL THF and added dropwise to 120 mL toluenewith stirring. p-Toluenesulfonic acid (30 mg) was added and the mixturerefluxed with water separation for 3 hours. Toluene was then evaporatedunder reduced pressure, the residue dissolved in ethyl acetate, andwashed in turn with water, and aqueous NaHCO₃. The ethyl acetatesolution was then dried and stripped to leave 0.3 g solid residue.Trituration with CHCl₃ :CH₃ OH (1:1) and filtration afforded 0.10 g ofthe title compound, m.p. 204°-206° C.

NMR (DMSO-d₆, 200 MHz) δ: 4.35 (t, 2H), 4.62 (t, 2H), 6.58 (d, 1H), 6.96(NHz), 7.26 (d, 1H). IR (nujol): 1715, 1725 sh, 3250, 3360 cm⁻¹.

EXAMPLE 63,4-Dihydro-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]-1-oxo-1H-pyrrolo[2,1-c][1,4]-oxazine-8-sulfonamide

A solution of 40 mg (0.185 mmol) of3,4-dihydro-1-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide and 53 mg(0.204 mmol) of phenyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamatein 0.8 mL acetonitrile was treated with 0.03 mL1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then stirred 40 minutes atambient temperature. Water (5 mL) plus 0.5 mL 1N HCl was added withstirring followed by ca. 1 mL of ethyl ether. The product crystallizedfrom the two phase mixture and was collected by filtration to afford 40mg of the title compound, m.p. 204°-207° C. dec.

NMR (DMSO-d₆, 200 MHz) δ: 2.48 (s, 3H), 3.98 (s, 3H), 4.38 (t, 2H), 4.62(t, 2H), 6.8 (d, 1H), 7.22 (d, 1H), 10.9 (NH), 12.45 (NH). IR (nujol):1725, 1705 sh cm⁻¹.

EXAMPLE 7 2-Amino-N-(1,1-dimethylethyl)benzenemethanesulfonamide

A mixture of 12 g (0.044 mol) ofN-(1,1-dimethylethyl)-2-nitrobenzenemethanesulfonamide and 1 g of 10%palladium on carbon in 175 mL ethanol was reduced by shaking in ahydrogen atmosphere at 50 psi for 30 minutes. The catalyst was removedby filtration through a pad of diatomaceous earth with ethanol rinsing.The filtrate was then evaporated under reduced pressure and the residuecrystallized from n-butyl chloride and hexanes to afford 10.1 g of thetitle compound, m.p. 115°-117° C.

NMR (CDCl₃, 200 MHz) δ: 1.38 (s, 3H), 3.5 (br, NH₂), 4.12 (s, NH), 4.29(s, 2H), 6.8 (m, 2H), 7.15 (m, 2H). IR (nujol): 3300, 3360, 3450 cm⁻¹.

EXAMPLE 8 N-(1,1-Dimethylethyl)-2-(formylamino)benzenemethanesulfonamide

Formic acetic anhydride was prepared by stirring a slurry of 34.4 g(0.42 mol) sodium formate in 35 mL ethyl ether and adding 24.9 mL (0.35mol) of acetyl chloride dropwise keeping the temperature at 25° C. withintermittent cooling. After vigorous stirring for 5 hours the slurry wasfiltered into another reaction vessel and diluted with 100 mL CH₂ Cl₂,then chilled to 0° C. A solution of 40 g (0.16 mol)2-amino-N-(1,1-dimethylethyl)benzenemethanesulfonamide in 200 mL CH₂ Cl₂was then added dropwise keeping the temperature below 10° C. The mixturewas then allowed to warm to room temperature and 50 mL methanol wasadded then stirred 18 hours. Evaporation of the solvent in vacuo left aresidue that was taken up in chloroform, washed two times with NaHCO₃solution, dried (MgSO₄) and stripped to dryness. The residue wastriturated with n-butyl chloride and hexanes (1:1) and collected byfiltration to afford 36.8 g of the title compound, m.p. 114°-115° C.

NMR (CDCl₃, 200 MHz) δ: 1.38 (s, 9H), 4.19 and 4.40 (NH), 4.31 and 4.33(s, 2H), 7.3 (m, 3H), 7.83 (d, 1H), 8.42 (s, 1H), 8.62 (NH). IR (nujol):1680, 3180, 3290 cm⁻¹.

EXAMPLE 9 N-(1,1-Dimethylethyl)-2-isocyanaobenzenemethanesulfonamide

A mixture of 33.6 g (0.124 mol) ofN-(1,1-dimethylethyl)-2-(formylamino)benzenemethanesulfonamide and 36.8mL (0.264 mol) triethylamine was stirred in 165 mL CH₂ Cl₂ and chilledto -10° C. under nitrogen atmosphere. To this solution was added asolution of 7.5 mL (0.062 mol) trichloromethyl chloroformate in 65 mLCH₂ Cl₂ dropwise over a 1 hour period, keeping the temperature less than0° C. The mixture was then stirred for 30 minutes at 0° C., then 1 hourat room temperature. After dilution with more CH₂ Cl₂, the mixture waswashed with water, then NaHCO₃ solution, dried over 4A molecular sievesand evaporated in vacuo. The residue was taken up in ethylacetate/hexane (1:1) and filtered through several hundred grams ofneutral alumina with ethyl acetate rinse and evaporated in vacuo. Thisresidue was triturated and collected with a mixture of n-butyl chlorideand hexane to afford 25.7 g of the title compound, m.p. 106°-108° C.

NMR (CDCl₃, 200 MHz) δ: 1.36 (s, 9H), 4.30 (NH), 4.45 (s, 2H), 7.42 (m,3H), 7.60 (m, 1H). IR (nujol): 3240, 2115, 1340, 1150, 1135 cm⁻¹.

EXAMPLE 10 N-(1,1-Dimethylethyl)-1H-indole-3-sulfonamide

A solution of 25.2 g (0.10 mol) ofN-(1,1-dimethylethyl)-2-isocyanobenzenemethanesulfonamide in 600 mLanhydrous THF was cooled to -70° C. under nitrogen atmosphere andtreated with 147 mL (0.22 mol) 1.5M lithium diisopropylamidemono(tetrahydrofuran) in cyclohexane at such a rate as to keep thetemperature under -60° C. The mixture was stirred at -70° C. for 15minutes then warmed to 0° C. Saturated ammonium chloride solution (75mL) was then added and the product was extracted with two 200 mLportions of ethyl acetate. The organic extract was washed with 10% HCl,brine, dried (MgSO₄) and evaporated in vacuo. The resulting residue wastriturated with ether/n-butyl chloride and collected by filtration toafford 22.7 g of the title compound, m.p. 157°-158° C.

NMR (CDCl₃, 200 MHz) δ: 1.23 (s, 9H), 4.60 (NH), 7.30 (m, 2H), 7.42 (m,1H), 7.72 (d, 1H). 7.89 (m, 1H), 8.78 (NH). IR (nujol): 3250, 3290 cm⁻¹.

EXAMPLE 11N-(1,1-Dimethylethyl)-1-[2-(tetrahydro-2-pyranyloxy)ethyl]-1H-indole-3-sulfonamide

A solution of 5.0 g (0.020 mol) ofN-(1,1-dimethylethyl)-1H-indole-3-sulfonamide in 30 mL anhydrous DMF wascooled to 10° C. under nitrogen atmosphere and was treated slowly with0.87 g (0.022 mol) 60% sodium hydride (oil dispersion). The mixture wasstirred for 20 minutes at room temperature then recooled to 10° C.,whereupon 5.0 g (0.024 mol) of 2-(2'-bromoethoxy)tetrahydropyran (J.Org. Chem., Vol. 50, p. 4243, 1985) was added followed by heating to 70°C. for 3 hours. After cooling in an ice bath, 20 mL of saturated NH₄ Clsolution plus 20 mL of water was added and the mixture was extractedtwice with ethyl acetate. The organic extract was washed twice withdilute HCl solution, then brine followed by drying (MgSO₄) andevaporation in vacuo. The residue was triturated and collected byfiltration with n-butyl chloride to afford 6.61 g of the title compound,m.p. 125°-132° C.

NMR (CDCl₃, 200 MHz) δ: 1.24 (s, 9H), 1.45 (m, 6H), 3.3-3.75 (m, 3H),4.02 (m, 2H), 4.3 (m, 2H), 4.5 (m, 2H), 7.3 (m, 3H), 7.76 (s, 1H), 7.87(m, 1H). IR (nujol): 1520, 3300 cm⁻¹.

EXAMPLE 123-[[(1,1-Dimethylethyl)amino]sulfonyl]-1-[2-(tetrahydro-2-pyranyloxy)ethyl]-1H-indole-2-carboxylicacid

A solution of 1.8 g (4.7 mmol) ofN-(1,1-dimethylethyl)-1-[2-(tetrahydro-2-pyranyloxy)-ethyl]-1H-indole-3-sulfonamidewas dissolved in 30 mL anhydrous THF and cooled to -60° C. undernitrogen atmosphere. To this was added dropwise, with stirring, 8.0 mL(12.8 mmol) 1.6M butyllithium in hexanes and the mixture allowed to warmto 0° C. for 20 minutes then recooled to -60° C. A large excess ofcrushed dry ice (4 g CO₂) was added all at once then the mixture wasstirred overnight at ambient temperature. Hydrochloric acid (1N, 15 mL)plus ice was then added and the mixture extracted three times with ethylacetate. The organic extracts were washed once with brine, dried (Na₂SO₄) and evaporated in vacuo. The solid residue was triturated andcollected by filtration with n-butyl chloride and hexane to afford 1.80g of the title compound, m.p. 149°-151° C. dec.

NMR δ: 1.21 (s, 9H), 1.3-1.8 (m, 6H), 3.3-4.9 (m, 9H), 7.4 (m, 3H), 8.32(d, 1H). IR (nujol): 1705, 3250 sh, 3100 sh cm⁻¹.

EXAMPLE 13

3-(Aminosulfonyl)-1-(2-hydroxyethyl)-1H-indole-2-carboxylic acid

To 50 mL acetone plus 1.80 g (4.2 mmol) of3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-[2-(tetrahydro-2-pyranyloxy)ethyl]1H-indole-2-carboxylicacid was added 4.2 mL 1N HCl and the mixture was stirred overnight.Acetone was then evaporated and the residue extracted with ethyl acetatethree times. The organic layer was washed once with brine, dried (Na₂SO₄) and stripped to dryness. The residue was then taken up intrifluoroacetic acid (20 mL) then evaporated in vacuo after severalhours at room temperature. The residue was triturated and collected withethyl ether to afford 1.37 g of the title compound, m.p. 145°-146° C.dec.

NMR (DMSO-d₆, 200 MHz) δ: 3.65 (t, 2H), 4.41 (t, 2H), 7.1 (NH₂), 7.3 (m,2H), 7.68 (d, 1H), 8.04 (d, 1H). IR (nujol): 1712, 3240, 3380, 3450cm⁻¹.

EXAMPLE 14 3,4-Dihydro-1-oxo-1H-[2,4]oxazino[4,3-a]indole-10-sulfonamide

To 100 mL benzene was added 0.40 g (1.4 mmol) of3-(aminosulfonyl)-1-(2-hydroxyethyl)-1H-indole-2-carboxylic acidfollowed by 20 mg of p-toluenesulfonic acid. The mixture was heated toreflux for 20 hours, cooled to room temperature, and the resultingprecipitate collected by filtration to afford 0.32 g of the titlecompound, m.p. 254°-260° C.

NMR (DMSO-d₆, 200 MHz) δ: 4.59 (t, 2H), 4.84 (t, 2H), 7.13 (NH₂), 7.33(t, 1H), 7.49 (t 1H), 7.72 (d, 1H), 8.79 (d, 1H). IR (nujol): 1700,3260, 3400 cm⁻¹.

EXAMPLE 153,4-Dihydro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-oxo-1H[1,4]oxazino[4,3-a]indole-10-sulfonamide

A 60 mg (0.23 mmol) sample of3,4-dihydro-1-oxo-1H-[1,4]oxazino[4,3-a]indole-10-sulfonamide wasdissolved in 1 mL dry acetonitrile and 70 mg (0.27 mmol) of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate was added. To this was added0.040 mL of DBU and the mixture was stirred at room temperature for 30minutes. A 0.2N solution of HCl was then added until the pH of themixture was less than 2. Additional water was added and the resultingprecipitate was collected by filtration and rinsed with water, thenethyl ether to afford 70 mg of the title compound, m.p. 206°-210° C.dec.

NMR (DMSO-d₆, 200 MHz) δ: 3.95 (s, 6H), 4.6 (t, 2H), 4.82 (t, 2H), 5.96(s, 1H), 7.4 (t, 1H), 7.52 (t, 1H), 7.76 (d, 1H), 8.24 (d, 1H), 10.41(NH), 12.77 (NH). IR (nujol): 1715, 1725 sh cm⁻¹.

By applying the procedures of Examples 1 through 15 and Equations 1through 17, the compounds in Tables 1 through 20 can be prepared by oneskilled in the art. In the following tables, abbreviations for variousalkyl chains and rings have been used with the following correspondingdefinitions.

    ______________________________________                                        Et         =     ethyl      =   CH.sub.2 CH.sub.3,                            iPr        =     isopropyl  =   CH(CH.sub.3).sub.2,                           nPr        =     n-propyl   =   CH.sub.2 CH.sub.2 CH.sub.3,                   cPr        =     cyclopropyl                                                                              =   CH(CH.sub.2).sub.2,                           cBu        =     cyclobutyl =   CH(CH.sub.2).sub.3,                           cC.sub.5 H.sub.9                                                                         =     cyclopentyl                                                                              =   CH(CH.sub.2).sub.4.                           ______________________________________                                    

                                      TABLE 1                                     __________________________________________________________________________     ##STR27##                                                                    R = R.sup.1 = R.sup.2 = H, Q = O, W = CH                                      X     Y        Z    X     Y         Z                                         __________________________________________________________________________    CH.sub.3                                                                            CH.sub.3 CH   NHCH.sub.3                                                                          OCH.sub.3 N                                         CH.sub.3                                                                            OCH.sub.3                                                                              CH   N(CH.sub.3).sub.2                                                                   OCH.sub.3 N                                         OCH.sub.3                                                                           OCH.sub.3                                                                              CH   C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                        N                                         Cl    OCH.sub.3                                                                              CH   NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                        N                                         CH.sub.3                                                                            OCH.sub.3                                                                              CCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                        N                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       CH   NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                      N                                         C.sub.2 H.sub.5                                                                     OCH.sub. 3                                                                             CH   N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                      N                                         H     OCH.sub.3                                                                              CH   CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        N                                         H     OC.sub.2 H.sub.5                                                                       CH   CF.sub.3                                                                            OCH.sub.3 N                                         OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                     CH   OCF.sub.2 H                                                                         OCH.sub.3 N                                         CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                    CH   CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    N                                         OCHF.sub.2                                                                          OCH.sub.3                                                                              CH   OCH.sub.3                                                                           CH.sub.3  CCl                                       OCH.sub.3                                                                           SCH.sub.3                                                                              CH   CH.sub.3                                                                            CH.sub.3  CCH.sub.3                                 OCH.sub.3                                                                           OCH.sub.3                                                                              CC.sub.2 H.sub.5                                               OCH.sub.3                                                                           CH.sub.3 CBr                                                            CH.sub.3                                                                            OCH.sub.3                                                                              N                                                              OCH.sub.3                                                                           OCH.sub.3                                                                              N                                                              __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = O, W = N                                                           R = R.sup.1 = R.sup.2 = H, Q = S, W = CH                  X     Y        Z    X     Y         Z                                         __________________________________________________________________________    CH.sub.3                                                                            CH.sub.3 CH   CH.sub.3                                                                            CH.sub.3  CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CH   CH.sub.3                                                                            OCH.sub.3 CH                                        OCH.sub.3                                                                           OCH.sub.3                                                                              CH   OCH.sub.3                                                                           OCH.sub.3 CH                                        Cl    OCH.sub.3                                                                              CH   Cl    OCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3 CCH.sub.3                                 CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       CH   CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        CH                                        C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                              CH   C.sub.2 H.sub.5                                                                     OCH.sub.3 CH                                        H     OCH.sub.3                                                                              CH   H     OCH.sub.3 CH                                        H     OC.sub.2 H.sub.5                                                                       CH   H     OC.sub.2 H.sub.5                                                                        CH                                        OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                     CH   OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                                        CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                    CH   CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                     CH                                        OCHF.sub.2                                                                          OCH.sub.3                                                                              CH   OCHF.sub.2                                                                          OCH.sub.3 CH                                        OCH.sub.3                                                                           SCH.sub.3                                                                              CH   OCH.sub.3                                                                           SCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              N    CH.sub.3                                                                            OCH.sub.3 N                                         OCH.sub.3                                                                           OCH.sub.3                                                                              N    OCH.sub.3                                                                           OCH.sub.3 N                                         NHCH.sub.3                                                                          OCH.sub.3                                                                              N    NHCH.sub.3                                                                          OCH.sub.3 N                                         N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                              N    N(CH.sub.3).sub.2                                                                   OCH.sub.3 N                                         C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                       N    C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                       N    NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                        N                                         N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                       N    N(CH.sub.3 ).sub.2                                                                  OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                     N    NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                      N                                         N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                     N    N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                      N                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       N    CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        N                                         CF.sub.3                                                                            OCH.sub.3                                                                              N    CF.sub.3                                                                            OCH.sub.3 N                                         OCF.sub.2 H                                                                         OCH.sub.3                                                                              N    OCF.sub.2 H                                                                         OCH.sub.3 N                                         CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                   N    CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    N                                         __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = S, W = N                                                           R = R.sup.1 = R.sup.2 = H, Q = NCH.sub.3, W = CH          X     Y        Z    X     Y         Z                                         __________________________________________________________________________    CH.sub.3                                                                            CH.sub.3 CH   CH.sub.3                                                                            CH.sub.3  CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CH   CH.sub.3                                                                            OCH.sub.3 CH                                        OCH.sub.3                                                                           OCH.sub.3                                                                              CH   OCH.sub.3                                                                           OCH.sub.3 CH                                        Cl    OCH.sub.3                                                                              CH   Cl    OCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CCH.sub.3                                                                          CH.sub. 3                                                                           OCH.sub.3 CCH.sub.3                                 CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       CH   CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        CH                                        C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                              CH   C.sub.2 H.sub.5                                                                     OCH.sub.3 CH                                        H     OCH.sub.3                                                                              CH   H     OCH.sub.3 CH                                        H     OC.sub.2 H.sub.5                                                                       CH   H     OC.sub.2 H.sub.5                                                                        CH                                        OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                     CH   OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                                        CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                    CH   CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                     CH                                        OCHF.sub.2                                                                          OCH.sub.3                                                                              CH   OCHF.sub.2                                                                          OCH.sub.3 CH                                        OCH.sub.3                                                                           SCH.sub.3                                                                              CH   OCH.sub.3                                                                           SCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              N    CH.sub.3                                                                            OCH.sub.3 N                                         OCH.sub.3                                                                           OCH.sub.3                                                                              N    OCH.sub.3                                                                           OCH.sub.3 N                                         NHCH.sub.3                                                                          OCH.sub.3                                                                              N    NHCH.sub.3                                                                          OCH.sub.3 N                                         N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                              N    N(CH.sub.3).sub.2                                                                   OCH.sub.3 N                                         C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                       N    C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                       N    NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                        N                                         N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                       N    N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OCH.sub.2 CF.sub. 3                                                                    N    NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                      N                                         N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                     N    N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                      N                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       N    CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        N                                         CF.sub.3                                                                            OCH.sub.3                                                                              N    CF.sub.3                                                                            OCH.sub.3 N                                         OCF.sub.2 H                                                                         OCH.sub.3                                                                              N    OCF.sub.2 H                                                                         OCH.sub.3 N                                         CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                   N    CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    N                                         __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = NH, W = CH                                                         R = R.sup.1 = R.sup.2 = H, Q = NH, W = N                  X     Y        Z    X     Y         Z                                         __________________________________________________________________________    CH.sub.3                                                                            CH.sub.3 CH   CH.sub.3                                                                            CH.sub.3  CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CH   CH.sub.3                                                                            OCH.sub.3 CH                                        OCH.sub.3                                                                           OCH.sub.3                                                                              CH   OCH.sub.3                                                                           OCH.sub.3 CH                                        Cl    OCH.sub.3                                                                              CH   Cl    OCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              CCH.sub.3                                                                          CH.sub.3                                                                            OCH.sub.3 CCH.sub.3                                 CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       CH   CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        CH                                        C.sub.2 H.sub.5                                                                     OCH.sub.3                                                                              CH   C.sub.2 H.sub.5                                                                     OCH.sub.3 CH                                        H     OCH.sub.3                                                                              CH   H     OCH.sub.3 CH                                        H     OC.sub.2 H.sub.5                                                                       CH   H     OC.sub.2 H.sub.5                                                                        CH                                        OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                     CH   OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                      CH                                        CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                    CH   CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                     CH                                        OCHF.sub.2                                                                          OCH.sub.3                                                                              CH   OCHF.sub.2                                                                          OCH.sub.3 CH                                        OCH.sub.3                                                                           SCH.sub.3                                                                              CH   OCH.sub.3                                                                           SCH.sub.3 CH                                        CH.sub.3                                                                            OCH.sub.3                                                                              N    CH.sub.3                                                                            OCH.sub.3 N                                         OCH.sub.3                                                                           OCH.sub.3                                                                              N    OCH.sub.3                                                                           OCH.sub.3 N                                         NHCH.sub.3                                                                          OCH.sub.3                                                                              N    NHCH.sub.3                                                                          OCH.sub.3 N                                         N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                              N    N(CH.sub.3).sub.2                                                                   OCH.sub.3 N                                         C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                       N    C.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                       N    NHCH.sub.3                                                                          OC.sub.2 H.sub.5                                                                        N                                         N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                       N    N(CH.sub.3).sub.2                                                                   OC.sub.2 H.sub.5                                                                        N                                         NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                     N    NHCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                      N                                         N(CH.sub.3).sub.2                                                                   OCH.sub. 2 CF.sub.3                                                                    N    N(CH.sub.3).sub.2                                                                   OCH.sub.2 CF.sub.3                                                                      N                                         CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                       N    CH.sub.3                                                                            OC.sub.2 H.sub.5                                                                        N                                         CF.sub.3                                                                            OCH.sub.3                                                                              N    CF.sub.3                                                                            OCH.sub.3 N                                         OCF.sub.2 H                                                                         OCH.sub.3                                                                              N    OCF.sub.2 H                                                                         OCH.sub.3 N                                         CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                   N    CH.sub.3                                                                            OCH.sub.2 CHCH.sub.2                                                                    N                                         __________________________________________________________________________    X = Y = OCH.sub.3                                                             R      R.sup.1                                                                              R.sup.2                                                                             O      W      Z                                           __________________________________________________________________________    H      Cl     H     O      CH     CH                                          H      Br     H     O      N      CH                                          H      CH.sub.3                                                                             H     NCH.sub.3                                                                            CH     N                                           CH.sub.3                                                                             H      H     O      CH     CH                                          H      H      CH.sub.3                                                                            O      CH     N                                           H      H      CH.sub.3                                                                            S      CH     CH                                          H      H      CH.sub.3                                                                            NCH.sub.3                                                                            N      N                                           __________________________________________________________________________    X = Y = OCH.sub.3, R = R.sup.1 = R.sup.2 = H                                  O                    W         Z                                              __________________________________________________________________________    NCH.sub.2 CH.sub.2 OCH.sub.3                                                                       N         N                                              NCH.sub.2 CH.sub.2 OEt                                                                             CH        N                                              NCH.sub.2 CF.sub.3   CH        CH                                             NCH.sub.2 CHF.sub.2  CH        N                                              N(CH.sub.2).sub.3 CCl.sub.3                                                                        CH        N                                              N(CH.sub.2).sub.3 Cl CH        CH                                             NEt                  CH        CH                                             NiPr                 CH        CH                                             NtBu                 N         CH                                             NCHF.sub.2           CH        N                                              NCH.sub.2 CCH        CH        CH                                             NCH.sub.2 OCH.sub.3  N         CH                                             __________________________________________________________________________    X = OCH.sub.3, Y = CH.sub.3                                                   R      R.sup.1                                                                              R.sup.2                                                                             O      W      Z                                           __________________________________________________________________________    H      Cl     H     O      CH     CH                                          H      Br     H     O      N      CH                                          H      CH.sub.3                                                                             H     NCH.sub.3                                                                            CH     N                                           CH.sub.3                                                                             H      H     O      CH     CH                                          H      H      CH.sub.3                                                                            O      CH     N                                           H      H      CH.sub.3                                                                            S      CH     CH                                          H      H      CH.sub.3                                                                            NCH.sub.3                                                                            N      N                                           H      H      H     O      CCH.sub.3                                                                            N                                           H      Cl     H     O      CCl    CH                                          H      Br     H     O      CBr    N                                           H      H      H     O      CCl    CH                                          H      Cl     H     O      N      CH                                          H      CH.sub.3                                                                             H     NCH.sub.3                                                                            N      N                                           __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = O, W = CH, Z = CH                              X         Y          X        Y                                               __________________________________________________________________________    (CH.sub.2).sub.3 CH.sub.3                                                               OCH.sub.3  OCH.sub.3                                                                              CH.sub.2 SO.sub.2 CH.sub.3                      iPr       OCH.sub.3  OCH.sub.3                                                                              cBu                                             (CH.sub.2).sub.4 Cl                                                                     OCH.sub.3  CH.sub.3 O(CH.sub.2).sub.2 CHCH.sub.2                    SEt       SEt        SCH.sub.2 CF.sub.3                                                                     OCH.sub.3                                       SCH.sub.3 OCH.sub.3  SCHF.sub.2                                                                             CH.sub.3                                        S(CH.sub.2).sub.3 CH.sub.3                                                              OCH.sub.3  CF.sub.3 CF.sub.3                                        OCH.sub.2 OEt                                                                           CH.sub.3   CH.sub.2 Cl                                                                            OCH.sub.3                                       O(CH.sub.2).sub.2 OiPr                                                                  OCH.sub.3  CH.sub.2 Br                                                                            OCH.sub.3                                       O(CH.sub.2).sub.2 OCH.sub.3                                                             OC.sub.2 H.sub.5                                                                         CH.sub.2 F                                                                             OEt                                             CH.sub.2 CH.sub.2 OCH.sub.3                                                             Et         I        OCH.sub.3                                       H         H          OCH.sub.2 CHF.sub.2                                                                    CH.sub.3                                        Cl        N(CH.sub.3).sub.2                                                                        NHiPr    CH.sub.3                                        Br        NHCH.sub.3 N(iPr).sub.2                                                                           CH.sub.3                                        OCH.sub.3 CN         OCH.sub.2 CF.sub.3                                                                     OCH.sub.2 CF.sub.3                              CH.sub.3  CH.sub.2 CCH                                                                             NEt.sub.2                                                                              NEt.sub.2                                       CH.sub.3  OCH.sub.2 CH.sub.2 CH                                                                    OCH.sub.3                                                                              N.sub.3                                         OCH.sub.3 OCH.sub.2 CHCH.sub.2                                                                     CH.sub.3 cPr                                             NEt.sub.2 OCH.sub.3  CH.sub.3 CH.sub.2 SEt                                    OCH.sub.2 iPr                                                                           OCH.sub.3  OCH.sub.3                                                                              CC.sub.5 H.sub.9                                NH.sub.2  CH.sub.3   O(CH.sub.2).sub.3 Cl                                                                   O(CH.sub.2).sub.3 Cl                            N(CH.sub.3)Et                                                                           OCH.sub.3                                                           Cl        OC.sub.2 H.sub.5                                                    Br        OCH.sub.3                                                           OCF.sub.2 H                                                                             OCF.sub.2 H                                                         OCH.sub.2 CF.sub.3                                                                      OCF.sub.2 H                                                         OCH.sub.2 CF.sub.3                                                                      CH.sub.3                                                            OCH.sub.2 CH.sub.2 CH.sub.2 F                                                           OCH.sub.3                                                           OiPr      OCH.sub.3                                                           CH.sub.3  N(OCH.sub.3)CH.sub.3                                                O(CH.sub.2).sub.3 CH.sub.3                                                              O(CH.sub.2).sub.3 CH.sub.3                                          iPr       iPr                                                                 OCH.sub.3 cPr                                                                 __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = O, W = CH, Z = N                               X                   Y                                                         __________________________________________________________________________    N(CH.sub.3).sub.2   N(CH.sub.3).sub.2                                         OEt                 NHnBu                                                     OCH.sub.3           NHiPr                                                     OCH.sub.2 F         NHtBu                                                     OCH.sub.3           OCF.sub.2 Br                                              NEt.sub.2           NEt.sub.2                                                 OCH.sub.3           NEt.sub.2                                                 OEt                 NHCH.sub.2 CF.sub.3                                       OCH.sub.3           N(CH.sub.2 CF.sub.3).sub.2                                OCH.sub.3           StBu                                                      OCH.sub.3           CN                                                        OCH.sub.3           N.sub.3                                                   OEt                 cPr                                                       OCH.sub.3           OCH.sub.2 CHCH.sub.2                                      CH.sub.3            CH.sub.3                                                  __________________________________________________________________________    R = R.sup.1 =  R.sup.2 = H, Q = O, W = CH                                      ##STR28##                                                                    X           R.sup.14       Z                                                  __________________________________________________________________________    CH.sub.3    CH.sub.3       CH                                                 OCH.sub.3   CH.sub.3       CH                                                 CH.sub.3    H              CH                                                 OCH.sub.3   H              CH                                                 CH.sub.3    (CH.sub.2).sub.2 CH.sub.3                                                                    CH                                                 CH.sub.3    CH.sub.3       N                                                  OCH.sub.3   CH.sub.3       N                                                  CH.sub.3    H              N                                                  OEt         H              CH                                                 OCH.sub.3   Et             N                                                  __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = O, W = CH                                       ##STR29##                                                                    X       R.sup.14                                                                              O.sup.3 R.sup.15                                                                      O.sup.4 R.sup.16                                                                       Z                                            __________________________________________________________________________    OCH.sub.3                                                                             CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                                                              CH                                           CH.sub.3                                                                              CH.sub.3                                                                              OCH.sub.3                                                                             OCH.sub.3                                                                              CH                                           OCH.sub.3                                                                             Et      OCH.sub.3                                                                             OCH.sub.3                                                                              N                                            OCH.sub.3                                                                             CH.sub.3                                                                              SEt     SEt      CH                                           CH.sub.3                                                                              CH.sub.3                                                                              S-nPr   SCH.sub.3                                                                              CH                                           OCH.sub.3                                                                             nPr     OCH.sub.3                                                                             OiPr     CH                                           __________________________________________________________________________    R =  R.sup.1 = R.sup.2 = H, Q = O, W = CH                                      ##STR30##                                                                    X      R.sup.14                                                                             O.sup.3                                                                              O.sup.4                                                                             p      Z                                           __________________________________________________________________________    OCH.sub.3                                                                            CH.sub.3                                                                             S      S     2      CH                                          CH.sub.3                                                                             CH.sub.3                                                                             O      O     2      CH                                          CH.sub.3                                                                             CH.sub.3                                                                             O      O     3      CH                                          OCH.sub.3                                                                            CH.sub.3                                                                             S      O     2      N                                           OEt    CH.sub.3                                                                             O      O     2      CH                                          OCH.sub.3                                                                            Et     S      O     3      N                                           __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = O, W = CH, Z = CH                               ##STR31##                                                                    X          R.sup.14  O.sup.3   O.sup.4                                        __________________________________________________________________________    OCH.sub.3  CH.sub.3  O         O                                              CH.sub.3   Et        O         O                                              OCH.sub.3  nPr       O         O                                              CH.sub.3   CH.sub.3  S         S                                              OCH.sub.3  Et        O         O                                              OCH.sub.3  CH.sub.3  S         O                                              __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR32##                                                                    R = R.sup.1 = R.sup.2 = H, Q = O                                              X    Y        Z    X    Y        Z                                            __________________________________________________________________________    CH.sub.3                                                                           CH.sub.3 CH   NHCH.sub.3                                                                         OC.sub.2 H.sub.5                                                                       N                                            CH.sub.3                                                                           OCH.sub.3                                                                              CH   N(CH.sub.3).sub.2                                                                  OC.sub.2 H.sub.5                                                                       N                                            OCH.sub.3                                                                          OCH.sub.3                                                                              CH   NHCH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                     N                                            Cl   OCH.sub.3                                                                              CH   N(CH.sub.3).sub.2                                                                  OCH.sub.2 CF.sub.3                                                                     N                                            CH.sub.3                                                                           OCH.sub.3                                                                              CCH.sub.3                                                                          CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       N                                            CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       CH   CF.sub.3                                                                           OCH.sub.3                                                                              N                                            C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                              CH   OCF.sub.2 H                                                                        OCH.sub. 3                                                                             N                                            H    OCH.sub.3                                                                              CH   CH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                   N                                            H    OC.sub.2 H.sub.5                                                                       CH                                                              OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                     CH                                                              CH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                    CH                                                              OCHF.sub.2                                                                         OCH.sub.3                                                                              CH                                                              OCH.sub.3                                                                          SCH.sub.3                                                                              CH                                                              CH.sub.3                                                                           OCH.sub.3                                                                              N                                                               OCH.sub.3                                                                          OCH.sub.3                                                                              N                                                               NHCH.sub.3                                                                         OCH.sub.3                                                                              N                                                               N(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                              N                                                               C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                       N                                                               __________________________________________________________________________    R = R.sup.1 = R.sup.2 = H, Q = NCH.sub.3                                                         R = R.sup.1 = R.sup.2 = H, Q = S                           X    Y        Z    X    Y        Z                                            __________________________________________________________________________    CH.sub.3                                                                           CH.sub.3 CH   CH.sub.3                                                                           CH.sub.3 CH                                           CH.sub.3                                                                           OCH.sub.3                                                                              CH   CH.sub.3                                                                           OCH.sub.3                                                                              CH                                           OCH.sub.3                                                                          OCH.sub.3                                                                              CH   OCH.sub.3                                                                          OCH.sub.3                                                                              CH                                           Cl   OCH.sub.3                                                                              CH   Cl   OCH.sub.3                                                                              CH                                           CH.sub.3                                                                           OCH.sub.3                                                                              CCH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                                                              CCH.sub.3                                    CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       CH   CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       CH                                           C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                              CH   C.sub.2 H.sub.5                                                                    OCH.sub.3                                                                              CH                                           H    OCH.sub.3                                                                              CH   H    OCH.sub.3                                                                              CH                                           H    OC.sub.2 H.sub.5                                                                       CH   H    OC.sub.2 H.sub.5                                                                       CH                                           OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                     CH   OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                     CH                                           CH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                    CH   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                    CH                                           OCHF.sub.2                                                                         OCH.sub.3                                                                              CH   OCHF.sub.2                                                                         OCH.sub.3                                                                              CH                                           OCH.sub.3                                                                          SCH.sub.3                                                                              CH   OCH.sub.3                                                                          SCH.sub.3                                                                              CH                                           CH.sub.3                                                                           OCH.sub.3                                                                              N    CH.sub.3                                                                           OCH.sub.3                                                                              N                                            OCH.sub.3                                                                          OCH.sub.3                                                                              N    OCH.sub.3                                                                          OCH.sub.3                                                                              N                                            NHCH.sub.3                                                                         OCH.sub.3                                                                              N    NHCH.sub.3                                                                         OCH.sub.3                                                                              N                                            N(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                              N    N(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                              N                                            C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                       N    C.sub.2 H.sub.5                                                                    OC.sub.2 H.sub.5                                                                       N                                            NHCH.sub.3                                                                         OC.sub.2 H.sub.5                                                                       N    NHCH.sub.3                                                                         OC.sub.2 H.sub.5                                                                       N                                            N(CH.sub.3).sub.2                                                                  OC.sub.2 H.sub.5                                                                       N    N(CH.sub.3).sub.2                                                                  OC.sub.2 H.sub.5                                                                       N                                            NHCH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                     N    NHCH.sub.3                                                                         OCH.sub.2 CF.sub.3                                                                     N                                            N(CH.sub.3).sub.2                                                                  OCH.sub.2 CF.sub.3                                                                     N    N(CH.sub.3).sub.2                                                                  OCH.sub.2 CF.sub. 3                                                                    N                                            CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       N    CH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       N                                            CF.sub.3                                                                           OCH.sub.3                                                                              N    CF.sub.3                                                                           OCH.sub.3                                                                              N                                            OCF.sub.2 H                                                                        OCH.sub.3                                                                              N    OCF.sub.2 H                                                                        OCH.sub.3                                                                              N                                            CH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                   N    CH.sub.3                                                                           OCH.sub.2 CHCH.sub.2                                                                   N                                            __________________________________________________________________________    X = Y = OCH.sub.3                                                             R     R.sup.1                                                                              R.sup.2                                                                             O     W     Z                                              __________________________________________________________________________    H     Cl     H     O     CH    CH                                             H     Br     H     O     N     CH                                             H     CH.sub.3                                                                             H     NCH.sub.3                                                                           CH    N                                              CH.sub.3                                                                            H      H     O     CH    CH                                             H     H      CH.sub.3                                                                            O     CH    N                                              H     H      CH.sub.3                                                                            S     CH    CH                                             H     H      CH.sub.3                                                                            NCH.sub.3                                                                           N     N                                              __________________________________________________________________________    X = CH.sub.3, Y = OCH.sub.3, R = R.sup.1 = R.sup.2 = H                        O             W           Z                                                   __________________________________________________________________________    NCH.sub.2 CH.sub.2 OCH3                                                                     N           N                                                   NCH.sub.2 CH.sub.2 OEt                                                                      CH          N                                                   NCH.sub.2 CF.sub.3                                                                          CH          CH                                                  NCH.sub.2 CHF.sub.2                                                                         CH          N                                                   N(CH.sub.2).sub.3 CCl.sub.3                                                                 CH          N                                                   N(CH.sub. 2).sub.3 Cl                                                                       CH          CH                                                  NEt           CH          CH                                                  NiPr          CH          CH                                                  NtBu          N           CH                                                  NCF.sub.2     CH          N                                                   NCH.sub.2 CCH CH          CH                                                  NCH.sub.2 OCH.sub.3                                                                         N           CH                                                  __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                         ##STR33##                                                                    R.sup.1 = R.sup.2 = H, Q = O,                                                                   R.sup.1 = R.sup.2 = H, Q = NCH.sub.3,                       W = CH            W = CH                                                      R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, Q = NH,                                                                  R.sup.1 = R.sup.2 = H, Q = O,                               W = CH            W = N                                                       R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, Q = S,                                                                   R.sup.1 = R.sup.2 = H, Q = NCH.sub.3,                       W = CH            W = N                                                       R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                         R.sup.1 = R.sup.2 = H, Q = NH,                                                                 R.sup.1 = CH.sub.3, R.sup.2 = H, Q = O,                     W = N             W W = N                                                     R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = Cl, R.sup.2 = H, Q = O,                                             W = CH                                                                        R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                         ##STR34##                                                                    R.sup.1 = H, R.sup.2 = CH.sub.3, Q = O, W = CH                                R        X           Y           Z                                            ______________________________________                                        H        CH.sub.3    CH.sub.3    CH                                           H        CH.sub.3    OCH.sub.3   CH                                           H        OCH.sub.3   OCH.sub.3   CH                                           H        Cl          OCH.sub.3   CH                                           CH.sub.3 OCH.sub.3   OCH.sub.3   CH                                           H        CH.sub.3    OCH.sub.3   N                                            H        OCH.sub.3   OCH.sub.3   N                                            H        NHCH.sub.3  OC.sub.2 H.sub.5                                                                          N                                            H        N(CH.sub.3).sub.2                                                                         OC.sub.2 H.sub.5                                                                          N                                            CH.sub.3 OCH.sub.3   OCH.sub.3   N                                            ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR35##                                                                    R.sup.1 = R.sup.2 = H, Q = O                                                                    R.sup.1 = R.sup.2 = H, Q = NCH.sub.3                        R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub. 3                                                                            OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, Q = S                                                  R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR36##                                                                    R.sup.1 = R.sup.3 = R.sup.4 = H,                                                               R.sup.1 = R.sup.3 = R.sup.4 = H,                             W = CH, n = 0    W = N, n = 1                                                 R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH   H    OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                        R.sup.1 = R.sup.3 = R.sup.4 = H,                                                               R.sup.1 = R.sup.4 = H, R.sup.3 = CH.sub.3,                   W = N, n = 0     n = 1, W = CH                                                R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH   H    OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                        R.sup.1 = R.sup.3 = R.sup.4 = H,                                                               R.sup.1 = H, R.sup.3 = R.sup.4 = CH.sub.3,                   n = 0, W = CH    n = 1, W = N                                                 R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub. 3                                                                            CH   H    OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                        R = H, X = Y = OCH.sub.3                                                      R.sup.1                                                                              R.sup.3  R.sup.4  n      W      Z                                      ______________________________________                                        H      H        Cl       1      N      N                                      Cl     H        H        0      CH     CH                                     H      Cl       Cl       1      N      CH                                     H      CH.sub.3 H        1      CH     N                                      H      F        F        0      CH     CH                                     H      Br       H        1      CH     CH                                     H      Br       CH.sub.3 1      CH     N                                      H      CH.sub.3 CH.sub.3 0      N      CH                                     ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR37##                                                                    R.sup.1 = R.sup.3 = R.sup.2 = H,                                                               R.sup.1 = R.sup.3 = R.sup.2 = H,                             W = CH, n = 1    W = N, n = 1                                                 R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH   H    OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR38##                                                                    R.sup.1 = R.sup.3 = R.sup.4 = H, n = 1                                                         R.sup.1 = R.sup.3 = R.sup.4 = H, n = 0                       R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH   H    OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                        R.sup.1 = R.sup.3 = H, R.sup.4 = CH.sub.3,                                    n = 1                                                                         R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                        R = H, X = CH.sub.3, Y = OCH.sub.3                                            R.sup.1 R.sup.3   R.sup.4   n        Z                                        ______________________________________                                        5-CH.sub.3                                                                            H         H         1        CH                                       4-Cl    H         H         0        N                                        H       F         H         1        CH                                       H       Cl        Cl        0        N                                        H       CH.sub.3  H         0        CH                                       H       H         Br        1        CH                                       H       F         F         0        N                                        ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR39##                                                                    R.sup.1 = R.sup.3 = R.sup.2 = H, n = 1                                                         R.sup.1 = R.sup.3 = R.sup.2 = H, n = 0                       R    X        Y       Z    R    X      Y      Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH   H    CH.sub.3                                                                             CH.sub.3                                                                             CH                              H    CH.sub.3 OCH.sub.3                                                                             CH   H    CH.sub.3                                                                             OCH.sub.3                                                                            CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH   H    OCH.sub.3                                                                            OCH.sub. 3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH   H    Cl     OCH.sub.3                                                                            CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH   CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             N    H    CH.sub.3                                                                             OCH.sub.3                                                                            N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N    H    OCH.sub.3                                                                            OCH.sub.3                                                                            N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N    H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                     N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N    H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                     N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                            N                               ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR40##                                                                    R.sup.1 = R.sup.2 = H,                                                                              R.sup.1 = R.sup.2 = H,                                  W = CH, Q.sup.1 = O   W = CH, Q.sup.1 = NH                                    R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H,                                                                              R.sup.1 = R.sup.2 = H,                                  W = CH, Q.sup.1 = NCH.sub.3                                                                         W = N, Q.sup.1 = NCH.sub.3                              R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H,                                                                              R.sup.1 = R.sup.2 = H, W = CH,                          W = N, Q.sup.1 = O    Q.sup.1 = NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3          R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub. 3                                                                           OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R = H, X = OCH.sub.3, Y = OCH.sub.3, Q.sup.1 = NR.sup.8                       R.sup.1                                                                              R.sup.2  R.sup.8        N      Z                                       ______________________________________                                        H      H        Et             CH     N                                       H      H        nC.sub.4 H.sub.9                                                                             N      CH                                      Cl     H        CH.sub.2 CF.sub.3                                                                            CH     CH                                      H      H        CH.sub.2 CHCH.sub.2                                                                          CH     N                                       H      H        CH.sub.2 CH.sub.2                                                                            CH     CH                                      CH.sub.3                                                                             H        CH.sub.2 OCH.sub.3                                                                           CH     N                                       H      CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                                                                  CH     CH                                      H      H        (CH.sub.2).sub.3 CH.sub.2 Cl                                                                 N      CH                                      H      H        CH(CH.sub.3)OEt                                                                              CH     CH                                      ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR41##                                                                    R.sup.1 = R.sup.2 = H, Q.sup.1 = O                                                                  R.sup.1 = R.sup.2 = H, Q.sup.1 = NCH.sub.3              R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub. 3                                                                          CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, Q.sup.1 = NH                                           R        X           Y             Z                                          ______________________________________                                        H        CH.sub.3    CH.sub.3      CH                                         H        CH.sub.3    OCH.sub.3     CH                                         H        OCH.sub.3   OCH.sub.3     CH                                         H        Cl          OCH.sub.3     CH                                         CH.sub.3 OCH.sub.3   OCH.sub.3     CH                                         H        CH.sub.3    OCH.sub.3     N                                          H        OCH.sub.3   OCH.sub.3     N                                          H        NHCH.sub.3  OC.sub.2 H.sub.5                                                                            N                                          H        N(CH.sub.3).sub.2                                                                         OC.sub.2 H.sub.5                                                                            N                                          CH.sub.3 OCH.sub.3   OCH.sub.3     N                                          ______________________________________                                        R = H, X = CH.sub.3, Y =  OCH.sub.3, Q.sup.1 = NR.sup.8                       R.sup.1  R.sup.2     R.sup.8       Z                                          ______________________________________                                        5-CH.sub.3                                                                             H           iPr           CH                                         H        H           CH.sub.2 CH(CH.sub.3).sub.2                                                                 N                                          5-Cl     H           H             CH                                         H        CH.sub.3    CH.sub.2 CHCH.sub.2                                                                         N                                          H        H           CH.sub.2 OCH.sub.3                                                                          N                                          H        H           CH.sub.2 CF.sub.3                                                                           CH                                         H        H           CHF.sub.2     N                                          ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR42##                                                                    R.sup.1 = R.sup.2 = H,                                                                              R.sup.1 = R.sup.2 = H,                                  W = CH, Q.sup.1 = NCH.sub.3                                                                         W = N, Q.sup.1 = NCH.sub.3                              R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, W = CH, Q.sup.1 = O                                    R        X            Y           Z                                           ______________________________________                                        H        CH.sub.3     CH.sub.3    CH                                          H        CH.sub.3     OCH.sub.3   CH                                          H        OCH.sub.3    OCH.sub.3   CH                                          H        Cl           OCH.sub.3   CH                                          CH.sub.3 OCH.sub.3    OCH.sub.3   CH                                          H        CH.sub.3     OCH.sub.3   N                                           H        OCH.sub.3    OCH.sub.3   N                                           H        NHCH.sub.3   OC.sub.2 H.sub.5                                                                          N                                           H        N(CH.sub.3).sub.2                                                                          OC.sub.2 H.sub.5                                                                          N                                           CH.sub.3 OCH.sub.3    OCH.sub.3   N                                           ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR43##                                                                    R.sup.1 = R.sup.2 = H, Q.sup.1 = NCH.sub.3                                                          R.sup.1 = R.sup.2 = H, Q.sup.1 = NH                     R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.2 = H, Q.sup.1 = O                                            R        X            Y           Z                                           ______________________________________                                        H        CH.sub.3     CH.sub.3    CH                                          H        CH.sub.3     OCH.sub.3   CH                                          H        OCH.sub.3    OCH.sub.3   CH                                          H        Cl           OCH.sub.3   CH                                          CH.sub.3 OCH.sub.3    OCH.sub.3   CH                                          H        CH.sub.3     OCH.sub.3   N                                           H        OCH.sub.3    OCH.sub.3   N                                           H        NHCH.sub.3   OC.sub.2 H.sub.5                                                                          N                                           H        N(CH.sub.3).sub.2                                                                          OC.sub.2 H.sub.5                                                                          N                                           CH.sub.3 OCH.sub.3    OCH.sub.3   N                                           ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR44##                                                                    R.sup.1 = H, n = 1,                                                                             R.sup.1 = H, n = 1,                                         m = 2, W = CH     m = 1, W = CH                                               R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, n = 0,                                                                             R.sup.1 = H, n = 1,                                         m = 2, W = CH     m = 2, W = N                                                R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, n = 0,                                                                             R.sup.1 = H, n = 1,                                         m = 2, W = CH     m = 1, W = N                                                R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub. 3                                                                             OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, n = 1,                                                                             R.sup.1 = CH.sub.3, n = 1,                                  m = 0, W = CH     m = 2, W = N                                                R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub. 3                                                                          N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, n = 1,                                                           m = 0, W = N                                                                  R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR45##                                                                    R.sup.1 = H, n = 1, m = 2                                                                       R.sup.1 = H, n = 1, m = 1                                   R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, n = 0, m = 0                                                     R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                         ##STR46##                                                                    R.sup.1 = R.sup.5 = H,                                                                          R.sup.1 = R.sup.5 = H,                                      Q.sup.2 = O, W = CH                                                                             Q.sup.2 = NCH.sub.3, W = CH                                 R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub. 3                                                                            CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.5 = H,                                                        Q.sup.2 = S, W = N                                                            R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                        R = H, X = CH.sub.3, Y = OCH.sub. 3                                           R.sup.1                                                                             R.sup.5 O.sup.2  W    Z                                                 ______________________________________                                        H     H       NCH.sub.3                                                                              N    CH                                                H     CH.sub.3                                                                              O        CH   N                                                 H     iPr     S        CH   N                                                 H     nPr     NCH.sub.3                                                                              N    CH                                                Cl    Et      O        CH   CH                                                ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                         ##STR47##                                                                    R.sup.1 = R.sup.5 = H, Q.sup.2 = O                                                              R.sup.1 = R.sup.5 = H, Q.sup.2 = NCH.sub.3                  R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub. 3                                                                            N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.5 = H, Q.sup.2 = S                                            R    X        Y         Z                                                     ______________________________________                                        H    CH.sub.3 CH.sub.3  CH                                                    H    CH.sub.3 OCH.sub.3 CH                                                    H    OCH.sub.3                                                                              OCH.sub.3 CH                                                    H    Cl       OCH.sub.3 CH                                                    CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3 CH                                                    H    CH.sub.3 OCH.sub.3 N                                                     H    OCH.sub.3                                                                              OCH.sub.3 N                                                     H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                        N                                                     H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                        N                                                     CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3 N                                                     ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                         ##STR48##                                                                    ______________________________________                                        R.sup.1 = R.sup.6 = H,                                                                          R.sup.1 = R.sup.6 = H,                                      n = 1, W = CH     n = 0, W = CH                                               R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub. 3                                                                           OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = R.sup.6 = H,                                                                          R.sup.1 = R.sup.6 = H,                                      n = 1, W = N      n = 0, W = N                                                R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub. 3                                                                              OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H,                                                                  R.sup.6 = CH.sub.3, n = 1, W = CH                                             R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                        R = H, X = OCH.sub.3, Y = OCH.sub.3                                           R.sup.1                                                                           R.sup. 6  n     W    Z                                                    ______________________________________                                        H   CH.sub.3  1     CH   N                                                    H   iPr       1     N    N                                                    H   OEt       1     CH   CH                                                   H   OCH.sub.3 0     CH   CH                                                   Cl  Cl        0     N    CH                                                   H   F         1     CH   N                                                    H   OC(O)CH.sub.3                                                                           0     CH   CH                                                   H   OC(O)Et   1     N    CH                                                   H   OSO.sub.2 CH.sub.3                                                                      1     CH   N                                                    H   OSO.sub.2 Et                                                                            0     N    CH                                                   H   OnPr      1     N    CH                                                   ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                         ##STR49##                                                                    ______________________________________                                        R.sup.1 = R.sup.6 = H, n = 1                                                                    R.sup.1 = R.sup.6 = H, n = 0                                R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub. 3                                                                          CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.1 = H, R.sup.6 = CH.sub.3, n = 1                                        R    X        Y       Z                                                       ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH                                                      H    CH.sub.3 OCH.sub.3                                                                             CH                                                      H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    Cl       OCH.sub.3                                                                             CH                                                      CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH                                                      H    CH.sub.3 OCH.sub.3                                                                             N                                                       H    OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N                                                       H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N                                                       CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N                                                       ______________________________________                                        R = H, X = CH.sub.3, Y = OCH.sub.3                                            R.sup.1                                                                             R.sup. 6  n      Z                                                      ______________________________________                                        H     OEt       0,     N                                                      H     OSO.sub.2 CH.sub.3                                                                      1      CH                                                     6-CH.sub.3                                                                          OCH.sub.3 1      CH                                                     H     Cl        1      N                                                      H     OC(O)CH.sub.3                                                                           0      CH                                                     ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                         ##STR50##                                                                    ______________________________________                                        R.sup.7 = CO.sub.2 CH.sub.3, n = 1                                                              R.sup.7 = CON(CH.sub. 3).sub.2, n = 1                       R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.7 = CO.sub.2 CH.sub.3, n = 0                                                              R.sup.7 = SO.sub.2 N(CH.sub.3).sub.2, n = 1                 R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R.sup.7 = SO.sub.2 CH.sub.3, n = 1                                                              R.sup.7 = SO.sub.2 N(CH.sub.3).sub.2, n = 0                 R    X        Y       Z     R    X      Y     Z                               ______________________________________                                        H    CH.sub.3 CH.sub.3                                                                              CH    H    CH.sub.3                                                                             CH.sub.3                                                                            CH                              H    CH.sub.3 OCH.sub.3                                                                             CH    H    CH.sub.3                                                                             OCH.sub.3                                                                           CH                              H    OCH.sub.3                                                                              OCH.sub.3                                                                             CH    H    OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    Cl       OCH.sub.3                                                                             CH    H    Cl     OCH.sub.3                                                                           CH                              CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             CH    CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           CH                              H    CH.sub.3 OCH.sub.3                                                                             N     H    CH.sub.3                                                                             OCH.sub.3                                                                           N                               H    OCH.sub.3                                                                              OCH.sub.3                                                                             N     H    OCH.sub.3                                                                            OCH.sub.3                                                                           N                               H    NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                      N     H    NHCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                    N                               H    N(CH.sub.3).sub.2                                                                      OC.sub.2 H.sub.5                                                                      N     H    N(CH.sub.3).sub.2                                                                    OC.sub.2 H.sub.5                                                                    N                               CH.sub.3                                                                           OCH.sub.3                                                                              OCH.sub.3                                                                             N     CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                           N                               ______________________________________                                        R = H, X = Y = OCH.sub.3                                                      R.sup.7  n      Z                                                             ______________________________________                                        CO.sub.2 Et                                                                            1      CH                                                            CO.sub.2 tBu                                                                           1      CH                                                            CO.sub.2 tBu                                                                           0      N                                                             CO.sub.2 iPr                                                                           1      CH                                                            C(O)NEt.sub.2                                                                          0      CH                                                            C(O)NHCH.sub.3                                                                         1      CH                                                            C(O)NHEt 0      N                                                             SO.sub.2 NEt.sub.2                                                                     1      CH                                                            SO.sub.2 NHCH.sub.3                                                                    0      CH                                                            SO.sub.2 NHEt                                                                          1      N                                                             SO.sub.2 CH.sub.3                                                                      1      CH                                                            SO.sub.2 nPr                                                                           0      CH                                                            SO.sub.2 Et                                                                            1      N                                                             SO.sub.2 CH.sub.3                                                                      0      N                                                             ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                         ##STR51##                                                                    R.sup.1 = R.sup.2 = R.sup.3 = R.sup.4 = R.sup.5 = R.sup.6 = H                 Q = Q.sup.2 = O, Q.sup.1 = NCH.sub.3                                          ______________________________________                                        L          A          X.sup.1     Y.sup.1                                     ______________________________________                                        L-1        A-2        CH.sub.3    O                                           L-1        A-2        OEt         O                                           L-2        A-2        OCH.sub.3   O                                           L-3        A-2        CH.sub.3    O                                           L-4        A-2        CH.sub.3    O                                           L-1        A-3        OCH.sub.3   --                                          L-5        A-3        OCH.sub.3   --                                          L-1        A-2        OCH.sub.3   CH.sub.2                                    L-1        A-2        OCF.sub.2 H O                                           L-2        A-2        OCH.sub.3   CH.sub.2                                    L-2        A-2        CH.sub.3    O                                           L-4        A-2        OCH.sub.3   CH.sub.2                                    L-1        A-3        CH.sub.3    --                                          L-5        A-3        OEt         --                                          ______________________________________                                        L          A          X.sup.1     Y.sup.3                                     ______________________________________                                        L-1        A-4        CH.sub.3    CH.sub.3                                    L-3        A-4        OCH.sub.3   H                                           L-8        A-4        CH.sub.3    CH.sub.3                                    L-2        A-4        CH.sub.3    CH.sub.3                                    L-4        A-4        CH.sub.3    H                                           L-7        A-4        CH.sub.3    H                                           ______________________________________                                        L          A          X.sup.2     Y.sup.2                                     ______________________________________                                        L-1        A-5        CH.sub.3    CH.sub.3                                    L-1        A-5        CH.sub.3    OCH.sub.3                                   L-3        A-5        CH.sub.2 CF.sub.3                                                                         OCH.sub.3                                   L-9        A-5        CH.sub.3    OCH.sub.3                                   L-11       A-5        CH.sub.3    OEt                                         L-1        A-5        CH.sub.3    SEt                                         L-2        A-5        CH.sub.3    Et                                          L-4        A-5        CH.sub.3    SCH.sub.3                                   L-10       A-5        Et          Et                                          L-12       A-5        CH.sub.3    OCH.sub.3                                   ______________________________________                                        L               A           X.sup.3                                           ______________________________________                                        L-1             A-6         CH.sub.3                                          L-7             A-6         CH.sub.3                                          L-2             A-6         OCH.sub.3                                         L-1             A-6         OCH.sub.3                                         L-8             A-6         OCH.sub.3                                         L-14            A-6         CH.sub.3                                          ______________________________________                                        L         A        X.sup.4    Y.sup.4 Z.sup.1                                 ______________________________________                                        L-1       A-7      CH.sub.3   CH.sub.3                                                                              CH                                      L-1       A-7      OCH.sub.3  CH.sub.3                                                                              CH.sub.3                                L-2       A-7      OCH.sub.3  OCH.sub.3                                                                             N                                       L-2       A-7      CH.sub.3   OEt     CH                                      L-3       A-7      Cl         CH.sub.3                                                                              CH                                      L-4       A-7      OEt        OEt     N                                       L-5       A-7      CH.sub.3   CH.sub.3                                                                              CH                                      L-7       A-7      CH.sub.3   CH.sub.3                                                                              CH                                      L-8       A-7      CH.sub.3   CH.sub.3                                                                              CH                                      L-15      A-7      CH.sub.3   OCH.sub.3                                                                             N                                       L-16      A-7      OCH.sub.3  OCH.sub.3                                                                             CH                                      L-12      A-7      CH.sub.3   CH.sub.3                                                                              N                                       ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

    ______________________________________                                                    Weight Percent*                                                               Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1963, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4; G. C. Klingman, "WeedControl as a Science", John Wiley and Sons, Inc., New York, 1961, pp.81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 16

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             99%                                                  triazin-2-y1)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      trimethylnonyl polyethylene glycol ether                                                               1%                                                   ______________________________________                                    

The surfactant is sprayed upon the active ingredient in a blender andthe mixture sifted through a U.S. Ser. No. 40 sieve (0.42 mm openings)prior to packaging. The concentrate may be formulated further forpractical use.

EXAMPLE 17

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                 65%                                                  pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide                                      dodecylphenol polyethylene glycol ether                                                                2%                                                   sodium ligninsulfonate   4%                                                   sodium silicoaluminate   6%                                                   montmorillonite (calcined)                                                                             23%                                                  ______________________________________                                    

The ingredients are thoroughly blended. The liquid surfactant is addedby spraying upon the solid ingredients in the blender. After grinding ina hammer mill to produce particles essentially all below 100 microns,the material is reblended and sifted through a U.S. Ser. No. 50 sieve(0.3 mm opening) and packaged.

EXAMPLE 18

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             50.0%                                                triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      polyacrylic acid thickener                                                                             0.3%                                                 dodecylphenol polyethylene glycol ether                                                                0.5%                                                 disodium phosphate       1%                                                   monosodium phosphate     0.5%                                                 polyvinyl alcohol        1.0%                                                 water                    56.7%                                                ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 19

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                35%                                                   pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide                                      blend of polyalcohol carboxylic esters                                                                6%                                                    and oil soluble petroleum sulfonates                                          xylene                  59%                                                   ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 3 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 20

    ______________________________________                                        Oil Suspension                                                                ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             25%                                                  triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      polyoxyethylene sorbitol hexaoleate                                                                    5%                                                   highly aliphatic hydrocarbon oil                                                                       70%                                                  ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 21

    ______________________________________                                        Aqueous Suspension                                                            ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                25%                                                   pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide                                      hydrated attapulgite    3%                                                    crude calcium ligninsulfonate                                                                         10%                                                   sodium dihydrogen phosphate                                                                           0.5%                                                  water                   61.5%                                                 ______________________________________                                    

The ingredients are ground together in a ball or roller mill until thesolid particles have been reduced to diameters under 10 microns.

EXAMPLE 22

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             40.0%                                                triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      dioctyl sodium sulfosuccinate                                                                          1.5%                                                 sodium ligninsulfonate   3%                                                   low viscosity methyl cellulose                                                                         1.5%                                                 attapulgite              54%                                                  ______________________________________                                    

The ingredients are thoroughly blended, passed through an air mill, toproduce an average particle size under 15 microns, reblended, and siftedthrough a U.S. Ser. No. 50 sieve (0.3 mm opening) before packaging.

All compounds of the invention may be formulated in the same manner.

EXAMPLE 23

    ______________________________________                                        Granule                                                                       ______________________________________                                        wettable powder of Example 22                                                                       15%                                                     gypsum                69%                                                     potassium sulfate     16%                                                     ______________________________________                                    

The ingredients are blended in a rotating mixer and water sprayed on toaccomplish granulation. When most of the material has reached thedesired range of 1.0 to 0.42 cm (U.S. Ser. No. #18 to 40 sieves), thegranules are removed, dried, and screened. Oversized material is crushedto produce additional material in the desired range. These granulescontain % active ingredient.

EXAMPLE 24

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                50%                                                   pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide                                      sodium alkylnaphthalenesulfonate                                                                      2%                                                    low viscosity methyl cellulose                                                                        2%                                                    diatomaceous earth      46%                                                   ______________________________________                                    

The ingredients are blended, coarsely hammermilled and the air milled toproduce particles of active essentially all below 10 microns indiameter. The product is reblended before packaging.

EXAMPLE 25

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             25%                                                  triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      anhydrous sodium sulfate 10%                                                  crude calcium ligninsulfonate                                                                          5%                                                   sodium alkylnaphthalenesulfonate                                                                       1%                                                   calcium/magnesium bentonite                                                                            59%                                                  ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S. Ser. No. 20 sieve (0.84 mm openings). The granules held on a U.S.Ser. No. 40 sieve (0.42 mm openings) may be packaged for use and thefines recycled.

EXAMPLE 26

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                80%                                                   pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide                                      sodium alkylnaphthalenesulfonate                                                                      2%                                                    sodium ligninsulfonate  2%                                                    synthetic amorphous silica                                                                            3%                                                    kaolinite               13%                                                   ______________________________________                                    

The ingredients are blended and then ground in a hammermill to produceparticles with an average particle size less than 25 microns indiameter. The material is reblended and sifted through a U.S. Ser. No.50 sieve (0.3 mm opening) before being packaged.

EXAMPLE 27

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             98.5%                                                triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide                                      silica aerogel           0.5%                                                 synthetic amorphous fine silica                                                                        1.0%                                                 ______________________________________                                    

The ingredients are blended and ground in a hammer mill to produce ahigh strength concentrate essentially all passing a U.S. Ser. No. 50sieve (0.3 mm openings). This material may then be formulated in avariety of ways.

EXAMPLE 28

    ______________________________________                                        Solution                                                                      ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-1,3,5-                                                             5%                                                   triazin-2-yl)amino]carbonyl]-1-oxo-1H-                                        pyrrolo[2,1-c][1,4]oxazine-8-sulfonamide,                                     sodium salt                                                                   water                    95%                                                  ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 29

    ______________________________________                                        Solution                                                                      ______________________________________                                        3,4-dihydro-N-[[(4-methoxy-6-methyl-2-                                                                5%                                                    pyrimidinyl)amino]carbonyl]-1-oxo-1H-                                         [1,4]oxazine[4,3-a]indole-10-sulfonamide,                                     sodium salt                                                                   water                   95%                                                   ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

Utility

Test results indicate that compounds of this invention are activepostemergence and preemergence herbicides or plant growth regulants.Several compounds in this invention are useful for the control ofselected grass and broadleaf weeds with tolerance to important agronomiccrops which include, but are not limited to cotton (Gossypium hirsutum),wheat (Triricum vulgaris), barley (Hordeum vulgare), sugar beets (Betavulgaris), and soybean (Glycine max). Grass and broadleaf weed speciescontrolled include, but are not limited to barnyardgrass (Echinochloacrus-galli), crabgrass (Digitaria spp.), cheatgrass (Bromus spp.),cocklebur (Xanthium pensylvanicum), and foxtail (Setaria spp.).

Weed control can be achieved with normal tillage, reduced tillage and notillage cropping systems.

These compounds also have utility for complete control and/or selectedcontrol of vegetation in specified areas such as around storage tanks,parking lots, highways, and railways, and in fallow crop, citrus, andplantation crop areas. Alternatively, these compounds may be useful tomodify plant growth and as citrus abscission agents.

An effective herbicidal amount of a compound from this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general terms, an effective amount of acompound from this invention is applied at rates from 0.001 to 20 kg/hawith a preferred rate range of 0.004 to 0.25 kg/ha. One skilled in theart can easily determine the application rate needed for the desiredlevel of weed control.

Compounds of this invention may be used alone or in combination withother commercial herbicides, insecticides, or fungicides. The followinglist exemplifies some of the herbicides suitable for use in mixtures. Acombination of a compound from this invention with one or more of thefollowing herbicides may be particularly useful for weed control.

    ______________________________________                                        Common Name                                                                              Chemical Name                                                      ______________________________________                                        acetochlor 2-chloro-N-(ethoxymethyl)-N-                                                  (2-ethyl-6-methylphenyl)acetamide                                  acifluorfen                                                                              5-[2-chloro-4-(trifluoromethyl)-                                              phenoxy]-2-nitrobenzoic acid                                       acrolein   2-propenal                                                         alachlor   2-chloro-N-(2,6-diethylphenyl)-N-                                             (methoxymethyl)acetamide                                           anilofos   S-4-chloro-N-isopropylcarbaniloyl-                                            methyl-O,O-dimethyl phosphorodi-                                              thioate                                                            ametryn    N-ethyl-N'-(1-methylethyl)-6-                                                 (methylthio)-1,3,5-triazine-2,4-                                              diamine                                                            amitrole   1H-1,2,4-triazol-3-amine                                           AMS        ammonium sulfamate                                                 asulam     methyl [(4-aminophenyl)sulfonyl]-                                             carbamate                                                          atrazine   6-chloro-N-ethyl-N'-(1-methylethyl)-                                          1,3,5-triazine-2,4-diamine                                         barban     4-chloro-2-butynyl 3-chlorocarbamate                               benefin    N-butyl-N-ethyl-2,6-dinitro-4-(tri-                                           fluoromethyl)benzenamine                                           bensulfuron                                                                              2-[[[[[(4,6-dimethoxy-2-pyrimi-                                    methyl     dinyl)amino]methylcarbonyl]-                                                  amino]sulfonyl]methyl]benzoic                                                 acid, methyl ester                                                 bensulide  O,O-bis(1-methylethyl) S-[2-                                                  [(phenylsulfonyl)amino]-                                                      ethyl]phosphorodithioate                                           bentazon   3-(1-methylethyl)-(1H)-2,1,3-                                                 benzothiadiazin-4(3H)-one,                                                    2,2-dioxide                                                        benzofluor N-[4-(ethylthio)-2-(trifluoro-                                                methyl)phenyl]methanesulfonamide                                   benzoylprop                                                                              N-benzoyl-N-(3,4-dichlorophenyl)-DL-                                          alanine                                                            bifenox    methyl 5-(2,4-dichlorophenoxy)-2-                                             nitrobenzoate                                                      bromacil   5-bromo-6-methyl-3-(1-methylpropyl)-                                          2,4(1H,3H)pyrimidinedione                                          bromoxynil 3,5-dibromo-4-hydroxybenzonitrile                                  butachlor  N-(butoxymethyl)-2-chloro-N-(2,6-                                             diethylphenyl)acetamide                                            buthidazole                                                                              3-[5-(1,1-dimethylethyl)-1,3,4-thia-                                          diazol-2-yl]-4-hydroxy-1-methyl-2-                                            imidazolidinone                                                    butralin   4-(1,1-dimethylethyl)-N-(1-methyl-                                            propyl)-2,6-dinitrobenzenamine                                     butylate   S-ethyl bis(2-methylpropyl)-                                                  carbamothioate                                                     cacodylic  dimethyl arsinic oxide                                             acid                                                                          CDAA       2-chloro-N,N-di-2-propenylacetamide                                CDEC       2-chloroallyl diethyldithiocarbamate                               CGA 142,464                                                                              3-(4,6-dimethoxy-1,3,5-triazin-2-yl)-                                         1-[2-(2-methoxyethoxy)-phenyl-                                                sulfonyl]-urea                                                     chloramben 3-amino-2,5-dichlorobenzoic acid                                   chlorbromuron                                                                            3-(4-bromo-3-chlorophenyl)-1-methoxy-1-                                       methylurea                                                         chlorimuron                                                                              2-[[[[(4-chloro-6-methoxy-2-pyrimi-                                ethyl      dinyl)ethylamino]carbonyl]-                                                   amino]sulfonyl]benzoic                                                        acid, ethyl ester                                                  chlormethoxy-                                                                            2,4-dichlorophenyl 4-nitro-3-                                      nil        methoxyphenyl ether                                                chlornitrofen                                                                            2,4,6-trichlorophenyl-4-nitro-                                                phenyl ether                                                       chloroxuron                                                                              N'-[4-(4-chlorophenoxy)phenyl]-N,N-                                           dimethylurea                                                       chlorpropham                                                                             1-methylethyl 3-chlorophenylcarbamate                              chlorsulfuron                                                                            2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-                                       triazin-2-yl)amino]carbonyl]benzene-                                          sulfonamide                                                        chlortoluron                                                                             N'-(3-chloro-4-methylphenyl)-N,N-                                             dimethylurea                                                       cinmethylin                                                                              exo-1-methyl-4-(1-methylethyl)-2-[(2-                                         methylphenyl)methoxy]-7-oxabicyclo-                                           [2.2.1]heptane                                                     clethodim  (E,E)-(±)-2-[1-[[(3-chloro-2-propenyl)-                                    oxy]imino]propyl]-5-[2-(ethylthio)-                                           propyl]-3-hydroxy-2-cyclohexen-1-one                               clomazone  2-[(2-chlorophenyl)methyl]-4,4-dimethyl-                                      3-isoxazolidinone                                                  cloproxydim                                                                              (E,E)-2-[1-[[(3-chloro-2-propenyl)oxy)-                                       imino]butyl]-5-[2-(ethylthio)propyl]-                                         3-hydroxy-2-cyclohexen-1-one                                       clopyralid 3,6-dichloro-2-pyridinecarboxylic acid                             CMA        calcium salt of MAA                                                cyanazine  2-[[4-chloro-6-(ethylamino)-1,3,5-tri-                                        azin-2-yl]amino]-2-methylpropanenitrile                            cycloate   S-ethyl cyclohexylethylcarbamothioate                              cycluron   3-cyclooctyl-1,1-dimethylurea                                      cyperquat  1-methyl-4-phenylpyridinium                                        cyprazine  2-chloro-4-(cyclopropylamino)-6-(iso-                                         propylamino)- .sub.-s-triazine                                     cyprazole  N-[5-(2-chloro-1,1-dimethylethyl)-1,3,4-                                      thiadiazol-2-yl]cyclopropanecarbox-                                           amide                                                              cypromid   3',4'-dichlorocyclopropanecarboxanilide                            dalapon    2,2-dichloropropanoic acid                                         dazomet    tetrahydro-3,5-dimethyl-2H-1,3,5-thia-                                        diazine-2-thione                                                   DCPA       dimethyl 2,3,5,6-tetrachloro-1,4-benzene-                                     dicarboxylate                                                      desmediphan                                                                              ethyl [3-[[(phenylamino)carbonyl]oxy]-                                        phenyl]carbamate                                                   desmetryn  2-(isopropylamino)-4-(methylamino)-6-                                         (methylthio)- .sub.-s-triazine                                     diallate   S-(2,3-dichloro-2-propenyl)bis(1-                                             methylethyl)carbamothioate                                         dicamba    3,6-dichloro-2-methoxybenzoic acid                                 dichlobenil                                                                              2,6-dichlorobenzonitrile                                           dichlorprop                                                                              (±)-2-(2,4-dichlorophenoxy)propanoic                                       acid                                                               dichlofop  (±)-2-[4-(2,4-dichlorophenoxy)phenoxy]-                                    propanoic acid, methyl ester                                       diethatyl  N-(chloroacetyl)-N-(2,6-diethylphenyl)-                                       glycine                                                            difenzoquat                                                                              1,2-dimethyl-3,5-diphenyl-1H-pyrazolium                            dimepiperate                                                                             S-1-methyl-1-phenylethylpiperidine-                                           1-carbothioate                                                     dinitramine                                                                              N.sup.3,N.sup.3 -diethyl-2,4-dinitro-6-(trifluoro-                            methyl)-1,3-benzenediamine                                         dinoseb    2-(1-methylpropyl)-4,6-dinitrophenol                               diphenamid N,N-dimethyl-α-phenylbenzeneacetamide                        dipropetryn                                                                              6-(ethylthio)-N,N'-bis(1-methylethyl)-                                        1,3,5-triazine-2,4-diamine                                         diquat     6,7-dihydrodipyrido[1,2-a:2',1'-c]-                                           pyrazinedium ion                                                   diuron     N'-(3,4-dichlorophenyl)-N,N-dimethylurea                           DNOC       2-methyl-4,6-dinitrophenol                                         DPX-M6316  3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-                                      2-yl)amino]carbonyl]amino]sulfonyl]-                                          2-thiophenecarboxylic acid, methyl                                            ester                                                              DSMA       disodium salt of MAA                                               dymron     N-(4-methylphenyl)-N'-(1-methyl-                                              1-phenylethyl)urea                                                 endothall  7-oxabicyclo[2.2.1]heptane-2,3-dicarbox-                                      ylic acid                                                          EPTC       S-ethyl dipropylcarbamothioate                                     esprocarb  S-benzyl-N-ethyl-N-(1,2-dimethyl)-                                 (SC2957)   propyl)thiolcarbamate                                              ethalfluralin                                                                            N-ethyl-N-(2-methyl-2-propenyl)-2,6-                                          dinitro-4-(trifluoromethyl)-                                                  benzenamine                                                        ethofumesate                                                                             (±)-2-ethoxy-2,3-dihydro-3,3-dimethyl-                                     5-benzofuranyl methanesulfonate                                    Express ®                                                                            2-[[[[N-(4-methoxy-6-methyl-1,3,5-                                            triazine-2-yl)-N-methylamino]-                                                carbonyl]  amino]sulfonyl]benzoic                                             acid, methyl ester                                                 fenac      2,3,6-trichlorobenzeneacetic acid                                  fenoxaprop (±)-2-[4-[(6-chloro-2-benzoxazolyl)oxy]-                                   phenoxy]propanoic acid                                             fenuron    N,N-dimethyl-N'-phenylurea                                         fenuron TCA                                                                              Salt of fenuron and TCA                                            flamprop   N-benzoyl-N-(3-chloro-4-fluorophenyl)-                                        DL-alanine                                                         fluazifop  (±)-2-[4-[[5-(trifluoromethyl)-2-pyri-                                     dinyl]oxy]phenoxy]propanoic acid                                   fluazifop-P                                                                              (R)-2-[4-[[5-(trifluoromethyl)-2-pyri-                                        dinyl]oxy]phenoxy]propanoic acid                                   fluchloralin                                                                             N-(2-chloroethyl)-2,6-dinitro-N-propyl-                                       4-(trifluoromethyl)benzenamine                                     fluometuron                                                                              N,N-dimethyl-N'-[3-(trifluoromethyl)-                                         phenyl]urea                                                        fluorochlor-                                                                             3-chloro-4-(chloromethyl)-1-[3-(tri-                               idone      fluoromethyl)phenyl]-2-pyrrolidinone                               fluorodifen                                                                               .sub.-p-nitrophenyl α,α,α-trifluoro-2-nitro-               1                                                                              .sub.-p-tolyl ether                                               fluorogly- carboxymethyl 5-[2-chloro-4-(tri-                                  cofen      fluoromethyl)phenoxy]-2-nitrobenzoate                              fluridone  1-methyl-3-phenyl-5-[3-(trifluoro-                                            methyl)phenyl]-4(1H)-pyridinone                                    fomesafen  5-[2-chloro-4-(trifluoromethyl)phenoxy]-                                      N-(methylsulfonyl)-2-nitrobenzamide                                fosamine   ethyl hydrogen (aminocarbonyl)-                                               phosphate                                                          glyphosate N-(phosphonomethyl)glycine                                         haloxyfop  2-[4-[[3-chloro-5-(trifluoromethyl)-2-                                        pyridinyl]oxy]phenoxy]propanoic acid                               hexaflurate                                                                              potassium hexafluoroarsenate                                       hexazinone 3-cyclohexyl-6-(dimethylamino)-1-methyl-                                      1,3,5-triazine-2,4(1H,3H)-dione                                    imazametha-                                                                              6-(4-isopropyl-4-methyl-5-oxo-2-                                   benz       imidazolin-2-yl)- .sub.-m-toluic acid,                                        methyl ester and 6-(4-isopropyl-                                              4-methyl-5-oxo-2-imidazolin-2-yl)-                                             .sub.-p-toluic acid, methyl ester                                 imazapyr   (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl-                                   ethyl)-5-oxo-1H-imidazol-2-yl]-3-                                             pyridinecarboxylic acid                                            imazaquin  2-[4,5-dihydro-4-methyl-4-(1-methyl-                                          ethyl)-5-oxo-1H-imidazol-2-yl]  -3-                                           quinolinecarboxylic acid                                           imazethapyr                                                                              (±)-2-[4,5-dihydro-4-methyl-4-(1-methyl-                                   ethyl)-5-oxo-1H-imidazol-2-yl]-5-                                             ethyl-3-pyridinecarboxylic acid                                    ioxynil    4-hydroxy-3,5-diiodobenzonitrile                                   isopropalin                                                                              4-(1-methylethyl)-2,6-dinitro-N,N-                                            dipropylbenzenamine                                                isoproturon                                                                              N-(4-isopropylphenyl)-N',N'-dimethylurea                           isouron    N'-[5-(1,1-dimethylethyl)-3-isoxazolyl]-                                      N,N-dimethylurea                                                   isoxaben   N-[3-(1-ethyl-1-methylpropyl)-5-                                              isoxazolyl]-2,6-dimethoxybenzamide                                 karbutilate                                                                              3-[[(dimethylamino)carbonyl]amino]-                                           phenyl-(1,1-dimethylethyl)carbamate                                lactofen   (±)-2-ethoxy-1-methyl-2-oxoethyl 5-[2-                                     chloro-4-(trifluoromethyl)phenoxy]-                                           2-nitrobenzoate                                                    lenacil    3-cyclohexyl-6,7-dihydro-1H-cyclopenta-                                       pyrimidine-2,4(3H,5H)-dione                                        linuron    N'-(3,4-dichlorophenyl)-N-methoxy-N-                                          methylurea                                                         MAA        methylarsonic acid                                                 MAMA       monoammonium salt of MAA                                           MCPA       (4-chloro-2-methylphenoxy)acetic acid                              MCPB       4-(4-chloro-2-methylphenoxy)butanoic                                          acid                                                               MON 7200   S,S-dimethyl-2-(difluoromethyl)-4-                                            (2-methylpropyl)-6-(trifluoromethyl)-                                         3,5-pyridinedicarbothionate                                        mecoprop   (±)-2-(4-chloro-2-methylphenoxy)-                                          propanoic acid                                                     mefenacet  2-(2-benzothiazolyloxy-N-methyl-N-                                            phenylacetamide                                                    mefluidide N-[2,4-dimethyl-5-[[(trifluoromethyl)-                                        sulfonyl]amino]phenyl]acetamide                                    methal-    N-(2-methyl-2-propenyl)-2,6-dinitro-N-                             propalin   propyl-4-(trifluoromethyl)benzenamide                              methabenz- 1,3-dimethyl-3-(2-benzothiazolyl)urea                              thiazuron                                                                     metham     methylcarbamodithioic acid                                         methazole  2-(3,4-dichlorophenyl)-4-methyl-1,2,4-                                        oxadiazolidine-3,5-dione                                           methoxuron N'-(3-chloro-4-methoxyphenyl)-N,N-                                            dimethylurea                                                       metolachlor                                                                              2-chloro-N-(2-ethyl-6-methylphenyl)-N-                                        (2-methoxy-1-methylethyl)acetamide                                 metribuzin 4-amino-6-(1,1-dimethylethyl)-3-(methyl-                                      thio)-1,2,4-triazin-5(4H)-one                                      metsulfuron                                                                              2-[[[[(4-methoxy-6-methyl-1,3,5-tri-                               methyl     azin-2-yl)amino]carbonyl]-                                                    amino]sulfonyl]benzoic acid,                                                  methyl ester                                                       MH         1,2-dihydro-3,6-pyridazinedione                                    molinate   S-ethyl hexahydro-1H-azepine-1-carbo-                                         thioate                                                            monolinuron                                                                              3-( .sub.-p-chlorophenyl)-1-methoxy-1-methyl-                                 urea                                                               monuron    N'-(4-chlorophenyl)-N,N-dimethylurea                               monuron TCA                                                                              Salt of monuron and TCA                                            MSMA       monosodium salt of MAA                                             napropamide                                                                              N,N-diethyl-2-(1-naphthalenyloxy)-                                            propanamide                                                        naptalam   2-[(1-naphthalenylamino)carbonyl]-                                            benzoic acid                                                       neburon    1-butyl-3-(3,4-dichlorophenyl)-1-methyl-                                      urea                                                               nitralin   4-(methylsulfonyl)-2,6-dinitro-N,N-                                           dipropylaniline                                                    nitrofen   2,4-dichloro-1-(4-nitrophenoxy)benzene                             nitrofluorfen                                                                            2-chloro-1-(4-nitrophenoxy)-4-(tri-                                           fluoromethyl)benzene                                               norea      N,N-dihmethyl-N',-(octahydro-4,7-methano-                                     1H-inden-5-yl)urea 3aα,-                                                4α,5α,7α,7aα-isomer                        norflurazon                                                                              4-chloro-5-(methylamino)-2-[3-(tri-                                           fluoromethyl)phenyl]-3(2H)-                                                   pyridazinone                                                       oryzalin   4-(dipropylamino)-3,5-dinitro-                                                benzenesulfonamide                                                 oxadiazon  3-[2,4-dichloro-5-(1-methylethoxy)-                                           phenyl]-5-(1,1-dimethylethyl)-                                                1,3,4-oxadiazol-2(3H)-one                                          oxyfluorfen                                                                              2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-                                       (trifluoromethyl)benzene                                           paraquat   1,1'-dimethyl-4,4'-dipyridinium ion                                pebulate   S-propyl butylethylcarbamothioate                                  pendimethalin                                                                            N-(1-ethylpropyl)-3,4-dimethyl-2,6-                                           dinitrobenzenamine                                                 perfluidone                                                                              1,1,1-trifluoro-N-[2-methyl-4-(phenyl-                                        sulfonyl)phenyl]methanesulfonamide                                 phenmedipham                                                                             3-[(methoxycarbonyl)amino]phenyl (3-                                          methylphenyl)carbamate                                             picloram   4-amino-3,5,6-trichloro-2-pyridine-                                           carboxylic acid                                                    PPG-1013   5-[2-chloro-4-(trifluoromethyl)-                                              phenoxy]-2-nitroacetophenone                                                  oxime-O-acetic acid, methyl ester                                  pretilachlor                                                                             α-chloro-2,6-diethyl-N-(2-propoxy-                                      ethyl)acetanilide                                                  procyazine 2-[[4-chloro-6-(cyclopropylamino)-1,3,5-                                      triazine-2-yl]amino]-2-methylpropane-                                         nitrile                                                            profluralin                                                                              N-(cyclopropylmethyl)-2,6-dinitro-N-                                          propyl-4-(trifluoromethyl)benzenamine                              prometon   6-methoxy-N,N'-bis(1-methylethyl)-1,3,5-                                      triazine-2,4-diamine                                               prometryn  N,N'-bis(1-methylethyl)-6-(methylthio)-                                       1,3,5-triazine-2,4-diamine                                         pronamide  3,5-dichloro-N-(1,1-dimethyl-2-propyn-                                        yl)benzamide                                                       propachlor 2-chloro-N-(1-methylethyl)-N-                                                 phenylacetamide                                                    propanil   N-(3,4-dichlorophenyl)propanamide                                  propazine  6-chloro-N,N'-bis(1-methylethyl)-                                             1,3,5-triazine-2,4-diamine                                         propham    1-methylethyl phenylcarbamate                                      prosulfalin                                                                              N-[[4-(dipropylamino)-3,5-dinitro-                                            phenyl]sulfonyl]-S,S-dimethylsulfil-                                          imine                                                              prynachlor 2-chloro-N-(1-methyl-2-propynyl)acet-                                         anilide                                                            pyrazolate 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-                                         pyrazol-5-yl- .sub.-p-toluenesulphonate                            pyrazon    5-amino-4-chloro-2-phenyl-3(2H)-                                              pyridazinone                                                       pyrazosulfuron                                                                           ethyl S-[3-(4,6-dimethoxypyrimidin-2-                              ethyl      yl)ureadosulfonyl]-1-methylpyrazole-                                          4-carboxylate                                                      quinclorac 3,7-dichloro-8-quinoline carboxylic acid                           quizalofop (±)-2-[4-[(6-chloro-2-quinoxalinyl)-                            ethyl      oxy]phenoxy]propanoic acid, ethyl                                             ester                                                              secbumeton N-ethyl-6-methoxy-N'-(1-methylpropyl)-                                        1,3,5-triazine-2,4-diamine                                         sethoxydim 2-[1-(ethoxyimino)butyl]-5-[2-(ethyl-                                         thio)propyl]-3-hydroxy-2-cyclohexen-                                          1-one                                                              siduron    N-(2-methylcyclohexyl)-N'-phenylurea                               simazine   6-chloro-N,N'-diethyl-1,3,5-triazine-                                         2,4-diamine                                                        SK-233     1-(α,α-dimethylbenzyl)-3-(4-methyl-                               phenyl)urea                                                        sulfometuron                                                                             2-[[[[(4,6-dimethyl-2-pyrimidinyl)-                                methyl     amino]carbonyl]amino]sulfonyl]-                                               benzoic acid, methyl ester                                         TCA        trichloroacetic acid                                               tebuthiuron                                                                              N-[5-(1,1-dimethylethyl)-1,3,4-thiadi-                                        azol-2-yl]-N,N'-dimethylurea                                       terbacil   5-chloro-3-(1,1-dimethylethyl)-6-                                             methyl-2,4(1H,3H)-pyrimidinedione                                  terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(1,1-                                          dimethylethyl)-6-methylphenyl]-                                               acetamide                                                          terbuthyl- 2-(tert-butylamino)-4-chloro-6-(ethyl-                             azine      amino)- .sub.-s-triazine                                           terbutol   2,6-di-tert-butyl- .sub.-p-toyl methylcar-                                    bamate                                                             terbutryn  N-(1,1-dimethylethyl)-N'-ethyl-6-                                             (methylthio)-1,3,5-triazine-                                                  2,4-diamine                                                        thiobencarb                                                                              S-[(4-chlorophenyl)methyl] diethylcar-                                        bamothioate                                                        triallate  S-(2,3,3-trichloro-2-propenyl) bis(1-                                         methylethyl)carbamothioate                                         triclopyr  [(3,5,6-trichloro-2-pyridinyl)-                                               oxy]acetic acid                                                    tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-                                              trichloroethyl)oxirane                                             trifluralin                                                                              2,6-dinitro-N,N-dipropyl-4-(tri-                                              fluoromethyl)benzenamine                                           trimeturon 1-( .sub.-p-chlorophenyl)-2,3,3-trimethylpseu-                                dourea                                                             2,4-D      (2,4-dichlorophenoxy)acetic acid                                   2,4-DB     4-(2,4-dichlorophenoxy)butanoic acid                               vernolate  S-propyl dipropylcarbamothioate                                    xylachlor  2-chloro-N-(2,3-dimethylphenyl)-N-                                            (1-methylethyl)acetamide                                           ______________________________________                                    

Herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. Test results and procedures follow.

COMPOUNDS

    ______________________________________                                         ##STR52##                                                                    COMPOUND  R      X        Y       Z    m.p. (°C.)                      ______________________________________                                         1        H      OCH.sub.3                                                                              OCH.sub.3                                                                             CH   221-223 (d)                             2        H      CH.sub.3 OCH.sub.3                                                                             N    204-207 (d)                             3        H      CH.sub.3 CH.sub.3                                                                              CH   202-205 (d)                             4        H      OCH.sub.3                                                                              CH.sub.3                                                                              CH   195-197 (d)                             5        H      OCH.sub.3                                                                              OCH.sub.3                                                                             N    208-210 (d)                             6        H      Cl       OCH.sub.3                                                                             CH   197-200 (d)                             7        H      NHCH.sub.3                                                                             OCH.sub.2 CH.sub.3                                                                    N    234-237 (d)                            ______________________________________                                         ##STR53##                                                                    COMPOUND  R      X        Y      Z     m.p. (°C.)                      ______________________________________                                         8        H      CH.sub.3 OCH.sub.3                                                                            CH    225-227 (d)                             9        H      OCH.sub.3                                                                              OCH.sub.3                                                                            CH    206-210 (d)                            10        H      OCH.sub.3                                                                              CH.sub.3                                                                             N     209-212 (d)                            11        H      OCH.sub.3                                                                              OCH.sub.3                                                                            N     167-169 (d)                            12        H      Cl       OCH.sub.3                                                                            CH    118-125 (d)                            ______________________________________                                         ##STR54##                                                                    COMPOUND  R      X        Y      Z     m.p. (°C.)                      ______________________________________                                        13        H      CH.sub.3 OCH.sub.3                                                                            CH     95-98 (d)                             14        H      OCH.sub.3                                                                              OCH.sub.3                                                                            CH    173-175 (d)                            15        H      CH.sub.3 OCH.sub.3                                                                            N     160-162 (d)                            16        H      OCH.sub.3                                                                              OCH.sub.3                                                                            N     157-161 (d)                            17        H      Cl       OCH.sub.3                                                                            CH    195-198 (d)                            ______________________________________                                         ##STR55##                                                                    COM-                                     m.p.                                 POUND  Q.sup.1       X       Y      Z    (°C.)                         ______________________________________                                        18     NCH.sub.3     CH.sub.3                                                                              OCH.sub.3                                                                            CH   230-                                                                          231 (d)                              19     NCH.sub.3     OCH.sub.3                                                                             OCH.sub.3                                                                            CH   226-                                                                          229 (d)                              20     NCH.sub.3     CH.sub.3                                                                              OCH.sub.3                                                                            N    225-                                                                          227 (d)                              21     NCH.sub.3     OCH.sub.3                                                                             OCH.sub.3                                                                            N    217-                                                                          219 (d)                              22     NCH.sub.3     Cl      OCH.sub.3                                                                            N    221-                                                                          224 (d)                              23     NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                              OCH.sub.3                                                                            CH   108-                                                                          110 (d)                              24     NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            CH   112-                                                                          114 (d)                              25     NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                              OCH.sub.3                                                                            N    124-                                                                          125 (d)                              26     NCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        OCH.sub.3                                                                             OCH.sub.3                                                                            N    117-                                                                          179 (d)                              27     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                              CH.sub.3                                                                             CH   205-                                                                          207 (d)                              28     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 OCH.sub.3                                                                             CH.sub.3                                                                             CH   210-                                                                          212 (d)                              29     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 OCH.sub.3                                                                             OCH.sub.3                                                                            CH   211-                                                                          213 (d)                              30     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                              OCH.sub.3                                                                            N    201-                                                                          203 (d)                              31     NCH.sub.2 CH.sub.2 CH.sub. 3                                                                OCH.sub.3                                                                             OCH.sub.3                                                                            N    184-                                                                          186 (d)                              32     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 Cl      OCH.sub.3                                                                            CH   198-                                                                          200 (d)                              33     NCH.sub.2 CH.sub.2 CH.sub.3                                                                 OC.sub.2 H.sub.5                                                                      NHCH.sub.3                                                                           N    164-                                                                          166 (d)                              ______________________________________                                         ##STR56##                                                                    COMPOUND  Q       X        Y     Z     m.p. (°C.)                      ______________________________________                                        34        O       CH.sub.3 CH.sub.3                                                                            CH    206-208 (d)                            35        O       CH.sub.3 OCH.sub.3                                                                           CH    183-193 (d)                            36        O       OCH.sub.3                                                                              OCH.sub.3                                                                           CH    208-209 (d)                            37        O       CH.sub.3 OCH.sub.3                                                                           N     021-206 (d)                            38        O       OCH.sub.3                                                                              OCH.sub.3                                                                           N     207-208 (d)                            39        O       Cl       OCH.sub.3                                                                           CH    200-202 (d)                            40        O       NHCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                    N     189-191 (d)                            41        NCH.sub.3                                                                             CH.sub.3 OCH.sub.3                                                                           CH    187-189 (d)                            42        NCH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                           CH    214-216 (d)                            43        NCH.sub.3                                                                             CH.sub.3 OCH.sub.3                                                                           N      70-74 (d)                             44        NCH.sub.3                                                                             OCH.sub.3                                                                              OCH.sub.3                                                                           N     205-207 (d)                            ______________________________________                                         ##STR57##                                                                    COMPOUND   R      X       Y      Z     m.p. (°C.)                      ______________________________________                                        45         H      CH.sub.3                                                                              CH.sub.3                                                                             CH    231-233 (d)                            46         H      CH.sub.3                                                                              OCH.sub.3                                                                            CH    191-194 (d)                            47         H      OCH.sub.3                                                                             OCH.sub.3                                                                            CH    188-192 (d)                            48         H      OCH.sub.3                                                                             CH.sub.3                                                                             N     207-208 (d)                            49         H      OCH.sub. 3                                                                            OCH.sub.3                                                                            N     166-172 (d)                            50         H      Cl      OCH.sub.3                                                                            CH    198-202 (d)                            ______________________________________                                         ##STR58##                                                                    COMPOUND   R      X       Y      Z     m.p. (°C.)                      ______________________________________                                        51         H      CH.sub.3                                                                              OCH.sub.3                                                                            CH    149-150 (d)                            52         H      OCH.sub.3                                                                             OCH.sub.3                                                                            CH    219-220 (d)                            53         H      CH.sub.3                                                                              OCH.sub.3                                                                            N     199-200 (d)                            54         H      OCH.sub.3                                                                             OCH.sub.3                                                                            N     186-187 (d)                            ______________________________________                                         ##STR59##                                                                    COMPOUND   R      X       Y      Z     m.p. (°C.)                      ______________________________________                                        55         H      CH.sub.3                                                                              CH.sub.3                                                                             CH    209-210 (d)                            56         H      OCH.sub.3                                                                             OCH.sub.3                                                                            CH    215-216 (d)                            57         H      OCH.sub.3                                                                             OCH.sub.3                                                                            N     204-205 (d)                            58         H      Cl      OCH.sub.3                                                                            CH    200-201 (d)                            59         H      CH.sub.3                                                                              OCH.sub.3                                                                            CH    142-143 (d)                            60         H      CH.sub.3                                                                              OCH.sub.3                                                                            N     143-145 (d)                            ______________________________________                                         (d) Indicates melting with apparent decomposition.                       

TEST A

Seeds of barely (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), cheatgrass (Bromus secalinus), cocklebur (Xanthiumpensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass(Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoeaspp.), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycinemax), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti),wheat (Triticum aestivum), and wild oat (Avena fatua) and purplenutsedge (Cyperus rotundus) tubers were planted and treated preemergencewith test chemicals dissolved in a non-phytotoxic solvent. At the sametime, these crop and weed species were also treated with postemergenceapplications of test chemicals. Plants ranged in height from two toeighteen cm (two to three leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse forapproximately sixteen days, after which all species were compared tocontrols and visually evaluated. Plant response ratings, summarized inTable A, are based on a scale of 0 to 10 where 0 is no effect and 10 iscomplete control. A dash (-) response means no test result.

                                      TABLE A                                     __________________________________________________________________________            COMPOUND                                                              Rate (50 g/ha)                                                                        1  2 3 4  5  6  7 8  9  10 11                                                                              12                                                                              13                                                                              14 15                                                                              16                                                                              17                                                                              18 19 20                                                                              21                                                                              22                __________________________________________________________________________    POSTEMERGENCE                                                                 Barley  9  9 9 9  10 8  3 9  9  9  9 8 9 9  9 9 0 9  9  7 9 9                 Barnyardgrass                                                                         10 9 9 10 6  9  0 9  9  9  9 9 9 9  9 9 9 9         9                                                                             3                                                                             7                                                                             9                 Cheatgrass                                                                            9  9 9 10 10 9  7 9  9  9  9 9 9 9  9 9 5 8         9                                                                             9                                                                             9                                                                             9                 Cocklebur                                                                             10 9 9 9  9  9  0 -- -- 9  9 --                                                                              9 9  5 1 1 9         9                                                                             9                                                                             8                                                                             10                Corn    9  9 9 10 8  9  3 10 9  9  9 9 9 9  9 9 9 9         9                                                                             9                                                                             9                                                                             9                 Cotton  9  3 9 9  0  9  0 2  10 9  2 2 9 9  9 8 7 10        10                                                                            9                                                                             9                                                                             9                 Crabgrass                                                                             9  9 9 9  4  10 0 9  9  9  9 9 7 9  8 9 3 10        10                                                                            2                                                                             5                                                                             10                Giant foxtail                                                                         9  9 9 9  9  9  --                                                                              8  9  7  7 6 9 9  9 8 8 9         9                                                                             9                                                                             8                                                                             9                 Morningglory                                                                          9  7 9 9  1  10 0 8  9  10 9 8 9 10 8 6 5 9         10                                                                            5                                                                             4                                                                             10                Nutsedge                                                                              -- 6 --                                                                              9  2  10 0 9  2  9  9 9 8 5  5 0 0 10        10                                                                            5                                                                             4                                                                             10                Rice    9  9 9 9  9  9  7 9  9  9  9 9 9 9  9 9 9 9         9                                                                             6                                                                             9                                                                             9                 Sorghum 9  9 9 9  9  9  6 9  9  9  9 9 9 9  9 9 9 9         9                                                                             9                                                                             9                                                                             10                Soybean 9  2 9 9  0  9  0 8  8  9  9 4 7 9  9 9 0 9         9                                                                             4                                                                             7                                                                             9                 Sugar beet                                                                            10 9 9 10 9  9  6 9  9  9  7 9 9 10 9 8 3 10        10                                                                            9                                                                             9                                                                             9                 Velvetleaf                                                                            10 3 9 9  0  9  0 2  3  9  7 7 9 10 7 8 6 9         9                                                                             5                                                                             7                                                                             9                 Wheat   9  9 8 9  7  8  6 9  9  9  9 9 8 9  9 9 0 9         9                                                                             9                                                                             9                                                                             9                 Wild oat                                                                              9  9 9 10 10 8  8 9  9  9  9 9 9 9  9 9 0 9         9                                                                             9                                                                             9                                                                             8                 PREEMERGENCE                                                                  Barley  9  7 6 8  0  7  0 5  2  7  0 2 0 0  0 0 0 0  8  0 0 9                 Barnyardgrass                                                                         9  7 3 4  0  8  0 9  9  9  3 6 0 7  0 0 0 2         0                                                                             1                                                                             1                                                                             3                 Cheatgrass                                                                            8  7 7 8  6  8  0 7  6  8  0 4 0 7  1 0 0 7         9                                                                             0                                                                             0                                                                             9                 Cocklebur                                                                             9  --                                                                              1 9  7  8  0 1  3  6  1 0 0 -- --                                                                              4 0 3         --                                                                            5                                                                             3                                                                             2                 Corn    9  7 9 9  0  9  0 9  2  8  2 3 0 2  1 2 1 7         8                                                                             2                                                                             0                                                                             9                 Cotton  8  0 0 0  0  0  0 5  5  8  2 2 0 2  0 0 0 2         5                                                                             0                                                                             0                                                                             0                 Crabgrass                                                                             9  5 9 9  1  9  0 8  8  8  9 8 0 9  2 0 0 5         9                                                                             6                                                                             4                                                                             9                 Giant foxtail                                                                         9  9 9 9  6  9  2 7  8  5  2 2 0 8  2 2 2 5         9                                                                             4                                                                             2                                                                             9                 Morningglory                                                                          9  0 9 9  0  8  0 4  0  9  8 7 0 0  0 0 0 2         2                                                                             0                                                                             1                                                                             2                 Nutsedge                                                                              9  0 9 10 0  9  0 6  0  7  0 0 0 0  0 0 0 5         9                                                                             0                                                                             0                                                                             0                 Rice    9  8 9 9  8  9  0 8  0  8  4 9 0 8  2 3 0 9         9                                                                             2                                                                             5                                                                             9                 Sorghum 9  8 9 9  2  9  0 9  5  9  8 9 1 8  1 2 1 2         9                                                                             0                                                                             0                                                                             9                 Soybean 8  1 2 6  0  5  0 4  0  3  2 5 1 2  1 0 2 3         8                                                                             3                                                                             4                                                                             5                 Sugar beet                                                                            9  8 9 9  0  9  0 8  8  9  8 8 3 8  2 2 2 6         8                                                                             0                                                                             0                                                                             9                 Velvetleaf                                                                            9  0 6 8  0  8  3 7  8  9  8 6 0 4  1 0 0 0         2                                                                             1                                                                             0                                                                             2                 Wheat   8  7 4 7  0  2  0 7  2  8  6 3 0 3  0 0 0 4         8                                                                             3                                                                             0                                                                             8                 Wild oat                                                                              8  2 5 7  3  3  0 6  2  5  2 4 0 2  0 2 0 0         5                                                                             0                                                                             0                                                                             1                 __________________________________________________________________________            COMPOUND                                                              Rate (10 g/ha)                                                                        1  2 3 4  5  6  7 8  9  10 11                                                                              12                                                                              13                                                                              14 15                                                                              16                                                                              17                                                                              18 19 20                                                                              21                                                                              22                __________________________________________________________________________    POSTEMERGENCE                                                                  Barley 9  9 7 9  8  7  0 8  7  9  9 6 7 9  3 8 0 9  9  0 1 9                 Barnyardgrass                                                                         9  9 6 10 0  9  0 9  9  9  9 9 5 9  8 7 7 7         9                                                                             0                                                                             0                                                                             8                 Cheatgrass                                                                            9  9 8 10 5  9  3 8  7  9  9 8 2 9  8 8 3 9         9                                                                             5                                                                             6                                                                             9                 Cocklebur                                                                             9  7 9 9  1  9  0 5  6  9  8 4 5 9  0 1 1 9         9                                                                             3                                                                             5                                                                             9                 Corn    10 9 9 9  8  9  0 9  9  9  9 9 9 9  8 9 9 9         9                                                                             4                                                                             4                                                                             9                 Cotton  9  0 6 8  0  8  0 0  0  3  0 0 3 8  1 0 1 9         9                                                                             3                                                                             5                                                                             9                 Crabgrass                                                                             9  3 8 9  0  8  0 7  9  9  9 3 7 8  5 2 0 7         10                                                                            0                                                                             0                                                                             9                 Giant foxtail                                                                         9  9 9 9  9  9  6 7  9  5  1 0 6 9  3 8 2 7         8                                                                             7                                                                             3                                                                             9                 Morningglory                                                                          10 2 9 9  0  9  0 7  5  9  3 5 9 9  2 1 1 9         10                                                                            1                                                                             0                                                                             9                 Nutsedge                                                                              10 0 5 9  -- -- 0 0  0  9  0 0 3 9  0 0 0 5         6                                                                             0                                                                             0                                                                             5                 Rice    9  9 9 9  9  9  3 8  9  9  9 8 9 9  9 9 5 7         9                                                                             8                                                                             7                                                                             --                Sorghum 10 8 9 9  9  9  0 8  9  9  8 8 9 9  9 9 8 9         9                                                                             8                                                                             7                                                                             9                 Soybean 9  0 8 9  0  8  0 5  5  8  7 1 1 8  1 3 0 7         8                                                                             2                                                                             2                                                                             4                 Sugar beet                                                                            9  8 9 9  6  9  2 7  9  9  2 7 8 9  3 7 3 9         9                                                                             3                                                                             6                                                                             9                 Velvetleaf                                                                            9  0 9 9  0  9  0 0  0  8  0 0 7 9  3 4 2 9         9                                                                             3                                                                             0                                                                             9                 Wheat   9  9 6 6  7  0  0 9  8  9  9 8 7 9  9 9 0 9         9                                                                             6                                                                             4                                                                             7                 Wild oat                                                                              9  8 9 9  9  2  7 9  9  9  9 7 4 9  7 9 0 9         9                                                                             6                                                                             9                                                                             3                 PREEMERGENCE                                                                  Barley  8  2 0 3  0  0  0 0  0  2  0 0 0 0  0 0 0 0  5  0 0 5                 Barnyardgrass                                                                         2  2 0 2  0  0  0 2  0  7  2 0 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             0                 Cheatgrass                                                                            7  2 4 6  3  4  0 0  0  7  2 0 0 3  0 0 0 2         6                                                                             0                                                                             0                                                                             2                 Cocklebur                                                                             -- 7 0 -- -- 0  --                                                                              0  0  5  0 0 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             4                 Corn    8  2 2 8  0  7  0 0  0  2  1 0 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             3                 Cotton  3  0 0 0  0  0  0 0  0  2  0 0 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             0                 Crabgrass                                                                             8  0 2 8  0  9  0 5  4  5  5 8 0 6  0 0 0 2         8                                                                             0                                                                             0                                                                             0                 Giant foxtail                                                                         9  0 4 8  0  8  0 0  0  2  0 0 0 3  0 0 0 0         2                                                                             0                                                                             0                                                                             0                 Morningglory                                                                          8  0 0 7  0  1  0 1  0  2  2 3 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             3                 Nutsedge                                                                              8  --                                                                              9 0  0  0  0 0  2  5  0 0 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             0                 Rice    9  4 6 9  0  8  0 0  0  3  0 2 0 3  0 0 0 3         5                                                                             0                                                                             0                                                                             8                 Sorghum 9  1 2 9  0  9  0 2  0  5  2 3 0 2  0 0 0 0         0                                                                             0                                                                             0                                                                             8                 Soybean 7  0 0 3  0  0  0 0  0  0  0 3 0 0  0 0 0 2         3                                                                             0                                                                             0                                                                             5                 Sugar beet                                                                            5  7 3 8  0  7  0 3  7  6  5 6 0 5  0 0 0 2         2                                                                             0                                                                             0                                                                             3                 Velvetleaf                                                                            7  0 0 3  0  2  2 3  3  4  1 5 0 0  0 0 0 0         0                                                                             0                                                                             0                                                                             0                 Wheat   8  2 0 6  0  0  0 0  0  3  2 0 0 0  0 0 0 0         2                                                                             0                                                                             0                                                                             0                 Wild oat                                                                              6  2 2 2  0  0  0 0  0  2  0 0 0 0  0 0 0 0         2                                                                             0                                                                             0                                                                             0                 __________________________________________________________________________

Test B

Seeds of barley (Hordeum yulgare), barnyardgrass (Echinochloacrus-galli), blackgrass (Alopecurus myosuroides), cheatgrass (Bromussecalinus), chickweed (Stellaria media), cocklebur (Xanthiumpensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass(Digitaria spp.), bedstraw (Galium aparine), giant foxtail (Setariafaberii), lambsquarters (Chenopodium album), morningglory (Ipomoeahederacea), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghumbicolor), soybeam (Glycine max), sugar beet (Beta vulgaris), velvetleaf(Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat(Polygonum convolvulus), and wild oat (Avena fatua) and purple nutsedge(Cyperus rotundus) tubers were planted and treated preemergence withtest chemicals dissolved in a non-phytotoxic solvent. At the same time,these crop and weed species were also treated with postemergenceapplications of test chemicals. Plants ranged in height from two toeighteen cm (one to four leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for twelveto sixteen days, after which all species were compared to controls andvisually evaluated. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 10 where 0 is no effect and 10 is completecontrol. A dash (-) response means no test result.

    TABLE B       COMPOUND Rate (50                                       g/ha) 23 24 25     26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49     50 51 52 53 54 55 56 57 58 59 60       POSTEMERGENCE Barley 0 0 0 1 7 9 9 9 9 7 8 0 0 0 0 0 0 0 6 9 0 0 0 9 9 2      8 2 9 9 6 8 8 9  6 8 9 6 Barnyard- 0 1 0 0 2 8 9 9 9 8 7 0 0 0 1 0 0 2     5 9 2 0 0 9 9 3 7 6 9 10  4 8 9 9 9 9 9 9 grass Bedstraw 0 0 0 0 3 7 8 7     7 7 3 0 0 0 0 0 -- 0 3 6 0 0 0 8 9 2 2 2 8 10  5 5 10  10  7 10  9 5     Blackgrass 3 2 0 0 5 9 9 10  9 8 8 0 0 0 0 0 0 0 5 9 2 4 0 9 9 8 9 0 9 9     8 8 9 9 9 8 9 9 Cheatgrass 1 2 0 0 4 9 9 9 9 2 8 0 0 1 0 0 0 0 6 8 0 0 0     9 9 5 8 0 10  10  2 7 9 9 9 8 10  8 Chickweed 0 0 0 4 5 7 10  -- -- --     -- 3 0 0 2 2 3 0 4 9 0 0 0 9 10  0 4 0 10  10  5 6 10  10  8 10  10  7     Cocklebur -- -- 0 0 -- -- -- -- -- -- -- 0 2 -- 0 0 0 0 7 9 0 0 0 9 9 1     0 7 -- -- -- -- -- -- -- -- -- -- Corn 0 6 0 0 5 9 9 9 9 9 9 0 0 0 0 0 0     0 2 9 0 0 0 9 9 6 9 9 9 9 9 9 9 10  9 9 9 9 Cotton 1 0 0 0 0 9 9 3 4 9 2     2 0 0 0 0 0 0 2 9 0 0 0 9 9 0 0 4 9 10  5 3 9 10  1 9 9 5 Crabgrass 0 2     0 0 0 6 8 3 7 3 1 0 0 0 2 2 0 0 2 9 0 0 0 8 8 0 2 0 9 10  3 0 9 7 2 5 8     8 Giant fox- 0 0 0 0 5 9 9 9 8 9 8 0 0 0 2 3 2 0 8 8 2 0 0 9 9 6 9 4 8 9     7 0 9 10  8 9 9 9 tail Lambsquar- 3 2 0 0 7 9 9 4 5 8 5 0 0 0 0 0 0 -- 7     9 0 0 0 9 10  0 0 7 9 10  2 0 9 10  2 9 9 4 ters Morning- 0 3 0 0 5 9 9     9 8 9 1 0 0 0 0 0 0 0 9 9 1 1 0 9 10  1 0 2 10  10  2 1 9 9 2 9 9 2     glory Nutsedge 0 0 0 0 0 2 9 0 3 3 0 0 -- 0 5 0 0 0 0 9 0 0 0 7 9 0 0 0     8 8 0 0 8 8 2 5 5 0 Rape 1 7 2 2 7 10  10  8 8 10  0 0 0 0 0 0 0 0 9 9 0     0 1 9 9 3 2 8 10  9 8 7 10  9 8 10  10  10  Rice 0 2 0 0 3 9 9 9 9 9 9 0     0 0 0 0 0 0 9 9 0 0 0 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 Sorghum 0 2 0 0 7 9     9 9 9 9 9 0 0 0 2 0 0 0 8 9 0 0 0 9 9 7 9 8 9 9 8 8 9 9 7 9 9 9 Soybean     1 0 0 0 1 9 9 9 8 3 3 0 0 0 0 0 0 0 2 9 2 0 0 8 9 1 1 1 9 9 5 5 9 10  8     9 9 8 Sugar beet 2 2 5 2 2 5 7 3 9 8 3 0 3 5 4 2 2 7 8 9 4 5 3 9 9 1 0 6     9 9 7 4 10  9 8 10  9 8 Velvetleaf 1 0 0 0 1 7 9 3 2 8 1 0 1 8 0 0 0 0 6     9 0 0 0 8 9 1 0 3 9 9 1 0 9 10  5 10  9 4 Wheat 0 0 0 0 7 9 9 9 9 2 8 0     0 0 0 0 0 0 6 8 0 0 0 9 9 8 9 0 9 9 7 9 9 9 9 7 9 10  Wild 0 0 0 0 2 7 9     9 6 9 0 0 0 1 0 0 0 0 4 9 0 0 0 9 9 0 2 5 9 9 6 8 10  10  6 10  9 7     buckwheat Wild oat 1 5 0 0 5 9 10  10  10  0 8 0 0 0 0 0 0 0 3 9 0 0 0 9     9 0 3 0 10  9 8 9 9 9 7 2 9 4 PREEMERGENCE Barley 0 0 0 0 0 0 7 0 0 0 0     0 0 0 0 1 0 0 1 2 0 0  0 0 0 0 0 0 8 9 0 2 8 0 4 7 8 2 Barnyard- 0 0 0 0     0 1 6 0 0 4 0 0 0 0 0 0 0 0 2 6 0 0 0 0 6 0 0 0 8 9 1 0 9 8 7 9 9 2     grass Bedstraw 0 0 0 0 -- -- -- -- -- 0 0 0 0 0 0 0 0 0 0 4 0 0 6 0 2 0     0 0 2 6 0 0 2 8 0 7 4 7 Blackgrass 2 0 0 0 0 8 9 3 3 3 0 0 0 0 4 4 0 4 0     7 2 2 0 2 8 0 3 0 8 9 4 4 9 7 0 8 8 0 Cheatgrass 0 0 0 0 0 5 9 7 3 0 0 0     0 0 0 0 0 0 0 6 2 2 0 7 9 0 6 0 9 9 6 7 9 9 9 9 9 9 Chickweed -- 0 0 0 6     9 8 0 2 4 0 0 0 0 0 8 0 0 0 9 0 0 9 8 9 0 0 0 9 9 2 2 10  9 9 10  9 7     Cocklebur 0 -- 0 -- -- -- -- -- -- -- -- 0 -- -- 0 -- 0 6 0 -- 0 -- 0 0     -- 2 0 -- -- -- -- -- -- -- -- -- -- Corn 0 0 0 0 0 3 9 3 0 4 0 0 0 0 0     0 0 0 0 4 0 0 0 0 8 0 0 0 9 9 3 2 9 9 8 9 9 8 Cotton 0 0 0 0 0 1 0 0 0 0     0 0 0 0 0 0 0 0 -- 1 0 0 0 0 6 0 0 0 4 7 0 0 9 5 2 7 8 3 Crabgrass 0 0 0     0 0 6 8 7 0 4 2 -- -- 0 -- -- -- -- -- -- -- -- 0 0 4 0 0 0 7 9 3 0 8 9     9 9 9 5 Giant fox- 0 0 0 0 0 5 8 2 0 5 1 0 0 0 0 0 0 0 2 2 0 0 0 1 7 0 0     0 7 9 1 0 9 7 9 9 9 3 tail Lambsquar- 0 0 0 0 7 10  9 2 0 8 0 0 0 0 0 0     0 0 0 9 0 8 0 2 8 0 0 0 9 9 3 0 9 10  8 9 10  7 ters Morning- 0 0 0 0 0     1 0 4 0 1 0 0 0 0 0 0 0 0 7 2 0 0 0 1 3 0 0 2 8 9 0 0 9 6 4 9 6 0 glory     Nutsedge 0 0 -- 0 0 0 1 0 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 6 8 5     0 9 0 0 7 7 5 Rape 0 0 0 0 0 5 9 0 0 7 0 0 0 0 0 0 2 2 2 0 0 0 0 0 6 0 0     0 4 9 0 0 8 9 6 9 9 2 Rice 0 0 0 0 0 3 9 2 2 5 2 0 0 0 0 0 0 0 2 8 0 0 0     2 9 0 0 0 9 9 7 8 10  9 9 9 9 9 Sorghum 0 0 0 0 0 3 9 1 1 7 1 0 0 0 0 0     0 0 0 5 0 0 0 2 9 0 0 0 8 9 0 1 9 8 2 9 9 2 Soybean 0 0 0 0 0 4 4 3 0 2     0 0 0 0 0 0 0 0 7 5 0 0 0 0 7 0 0 0 9 9 0 0 9 9 7 9 9 5 Sugar beet 1 0 0     0 0 6 7 3 2 3 0 0 0 0 2 0 2 2 2 9 2 2 0 0 8 0 0 0 9 9 5 4 9 9 4 9 9 8     Velvetleaf 0 0 0 0 0 1 1 0 0 0 0 0 2 0 1 0 0 0 7 0 0 0 0 0 2 0 0 1 7 9 0     1 8 8 1 8 8 1 Wheat 0 0 0 0 0 2 9 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 7 0     0 0 9 9 2 2 9 9 2 5 9 8 Wild 0 0 0 0 2 5 5 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0     0 0 3 0 0 0 2 8 0 0 6 8 0 4 8 0 buckwheat Wild oat 0 0 0 0 0 3 8 0 0 0 0     0 0 0 2 0 0 0 0 3 0 0 0 0 8 0 0 0 9 8 0 3 8 2 2 0 8 3       COMPOUND Rate (10                                        g/ha) 23 24     25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48     49 50 51 52 53 54 55 56 57 58 59 60       POSTEMERGENCE Barley 0 0 0 0 3 8 9 8 8 5 6 0 0 0 0 0 0 0 0 7 0 0 0 6 9 0      4 0 7 9 0 3 3 8 3 3 5 0 Barnyard- 0 0 0 0 0 6 8 5 1 6 3 0 0 0 0 0 0 0 2     8 0 0 0 8 9 0 0 2 9 9 0 0 8 8 2 8 9 7 grass Bedstraw 0 0 0 0 0 6 7 6 3 6     0 0 0 0 0 0 0 0 0 5 0 0 0 5 8 0 0 0 7 10  0 2 4 8 3 5 5 3 Blackgrass 0 0     0 0 2 7 8 9 8 2 4 0 0 0 0 0 0 0 3 7 0 0 0 5 6 4 7 0 9 9 0 4 9 9 5 5 7 8     Cheatgrass 0 0 0 0 0 7 8 8 5 0 5 0 0 0 0 0 0 0 0 6 0 0 0 7 9 0 4 0 9 9 0     0 9 9 5 2 8 2 Chickweed 0 0 0 0 -- -- -- 0 0 5 5 0 0 0 0 0 0 0 0 5 0 0 0     6 10  0 0 0 9 10  0 0 -- -- -- -- -- 6 Cocklebur 0 -- 0 0 -- -- -- -- --     -- -- 0 0 -- 0 0 0 0 0 5 0 0 0 5 9 0 0 4 -- --  -- -- -- -- -- -- -- --     Corn 0 0 0 0 0 9 9 8 6 8 2 0 0 0 0 0 0 0 0 9 0 0 0 9 9 0 1 1 9 9 0 0 9 9     4 9 9 9 Cotton 0 0 0 0 0 8 9 1 2 1 1 2 0 0 0 0 0 0 2 9 0 0 0 8 9 0 0 0 9     9 0 0 9 9 0 9 9 0 Crabgrass 0 0 0 0 0 4 5 0 0 2 0 0 0 0 0 0 0 0 0 5 0 0     0 5 5 0 0 0 3 9 0 0 4 2 0 1 6 2 Giant fox- 0 0 0 0 2 8 9 8 2 7 3 0 0 0 0     0 0 0 3 7 0 0 0 8 9 2 1 2 5 8 0 0 8 9 4 7 9 5 tail Lambsquar- 0 0 0 0 4     8 8 0 0 8 0 -- 0 0 0 0 0 0 2 7 0 0 0 6 10  0 0 4 9 10  2 0 6 8 0 6 7 0     ters Morning- 0 0 0 0 1 9 9 3 3 7 1 0 0 0 0 0 0 0 0 9 0 0 0 8 10  0 0 0     9 10  1 0 9 5 1 9 9 1 glory Nutsedge 0 0 0 0 0 -- 5 0 0 0 0 0 0 0 0 0 0     0 0 8 0 0 0 2 9 0 -- 0 4 7 0 0 4 4 0 0 5 0 Rape 0 0 0 2 6 9 9 7 6 9 0 0     0 0 0 0 0 0 8 9 0 0 0 9 9 0 0 7 10  10  3 6 9 9 7 10  9 8 Rice 0 0 0 0 0     5 9 8 8 7 7 0 0 0 0 0 0 0 8 9 0 0 0 9 9 6 7 7 9 9 5 6 9 9 9 9 9 8     Sorghum 0 0 0 0 0 9 9 9 4 9 2 0 0 0 0 0 0 0 2 8 0 0 0 9 9 0 0 3 9 9 1 0     9 9 1 9 9 7 Soybean 0 0 0 0 0 8 9 3 2 2 1 0 0 0 0 0 0 0 3 7 0 0 0 6 9 0     0 0 9 9 0 0 9 9 2 8 9 3 Sugar beet 0 0 0 0 0 5 2 2 2 6 2 0 2 0 2 1 2 2 6     8 2 2 0 8 9 0 0 2 8 9 3 3 9 9 7 10  8 7 Velvetleaf 0 0 0 0 0 5 6 0 1 3 0     0 0 0 0 0 0 0 2 8 0 0 0 7 9 0 0 1 9 9 0 0 8 9 1 8 9 0 Wheat 0 0 0 0 2 8     7 8 8 0 7 0 0 0 0 0 0 0 2 6 0 0 0 7 9 2 6 0 8 9 0 4 9 9 6 2 8 8 Wild 0 0     0 0 0 6 7 2 2 7 0 0 0 0 0 0 0 0 3 8 0 0 0 7 6 0 0 0 9 8 0 3 9 9 5 8 7 5     buckwheat Wild oat 0 2 0 0 0 8 8 9 8 0 7 0 0 0 0 0 0 0 2 7 0 0 0 5 9 0 2     0 8 9 2 4 2 9 0 0 7 0 PREEMERGENCE Barley 0 0 0 0 0 0 2 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 0 0 2 9 0 0 0 0 0 2 2 0 Barnyard- 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 2 0 0 0 0 2 0 0 2 5 1 8 3 1 grass     Bedstraw 0 0 0 0 -- -- -- -- 2 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 0 0 0 0 0 0     0 0 0 2 0 0 0 0 Blackgrass 0 0 0 0 0 2 4 0 0 0 0 0 0 0 2 2 0 0 0 3 0 2 0     0 2 0 0 0 0 8 0 0 9 2 0 4 3 0 Cheatgrass 0 0 0 0 0 3 8 0 2 0 0 0 0 0 0 0     0 0 0 3 0 0 0 0 4 0 2 0 8 9 0 0 9 3 4 6 8 2 Chickweed 0 0 0 0 0 -- 8 --     9 -- 0 0 0 0 0 0 -- 0 -- 7 0 0 -- 0 -- 0 0 0 7 9 0 0 10  9 2 10  8 5     Cocklebur 0 -- 0 0 -- -- -- -- -- -- -- 0 -- -- -- 0 0 0 0 -- -- -- 0 0     0 -- 0 0 -- -- -- -- -- -- -- -- -- -- Corn 0 0 0 0 0 0 6 0 0 0 0 0 0 0     0 0 0 0 0 1 0 0 0 0 3 0 0 0 2 9 0 0 9 3 2 8 5 2 Cotton 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 5 0 0 5 1 0 0 0 0 Crabgrass 0 0     0 0 0 3 6 0 0 0 0 -- -- 0 -- -- -- -- -- -- -- -- 0 0 1 0 0 0 0 7 0 0 4     0 5 6 2 0 Giant fox- 0 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0     0 0 0 3 0 0 3 2 0 6 1 0 tail Lambsquar- 0 0 0 0 2 7 8 0 0 0 0 -- 0 -- 0     0 0 0 0 3 0 -- -- 0 -- 0 0 0 8 8 0 0 8 9 0 5 9 2 ters Morning- 0 0 0 0 0     0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 1 3 0 0 7 1 0 -- 5 0 glory     Nutsedge 0 0 0 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 Rape 0 0 0 0 0 0 7 0 0 0 0 0 0 0 0 0 2 2 0 0 0 0 0 0 0 0 0     0 0 6 0 0 5 4 2 2 2 0 Rice 0 0 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0     0 7 0 0 0 6 9 0 2 9 6 2 9 8 7 Sorghum 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0     0 0 0 0 0 0 0 2 0 0 0 0 7 0 0 7 2 0 7 1 0 Soybean 0 0 0 0 0 0 1 0 0 0 0     0 0 0 0 0 0 0 0 1 0 0 0 0 2 0 0 0 2 8 0 0 6 5 0 4 3 2 Sugar beet 0 0 0 0     0 2 2 2 4 2 0 0 0 0 0 0 0 2 2 2 0 2 0 0 3 0 0 0 7 9 2 2 8 7 5 7 7 3     Velvetleaf 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0     0 2 1 0 3 2 0 Wheat 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0     0 0 6 9 0 0 9 0 0 0 6 3 Wild 0 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0     0 0 2 0 0 0 0 2 0 0 2 0 0 0 0 0 buckwheat Wild oat 0 0 0 0 0 0 2 0 0 0 0     0 0 0 0 0 0 0 0 2 0 0 0 0 3 0 0 0 5 8 0 0 3 0 0 0 2 0

Test C

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellariamedia), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromustectorum), giant foxtail (Setaria faberi), green foxtail (Setariaviridis), jimsonweed (Datura stramonium), johnsongrass (Sorghumhalepense), lambsquarters (Chenopodium album), morningglory (Ipomoeaspp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassiaobtusifolia), soybeam (Glycine max), sugar beet (Beta vulgaris), teaweed(Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Triticumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted andtreated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to eighteen cm (two to three leaf stage) forpostemergence treatments. Treated plants and controls were maintained ina greenhouse for approximately 24 days, after which all species werecompared to controls and visually evaluated. Plant response ratings,summarized in Table C, are reported on a 0 to 10 scale where 0 is noeffect and 10 is complete control. A dash (-) esponse means no testresult.

                                      TABLE C                                     __________________________________________________________________________               COMPOUND                                                                                                                     Rate                           Rate (250 g/ha)                                                                        Rate (62 g/ha)                                                                              Rate (16 g/ha)                                                                            Rate (4 g/ha)                                                                             (1 g/ha)                       2  8 10                                                                              11                                                                              1  2 8 9 10                                                                              11 1 2 8 9 10                                                                              11                                                                              1 2 8 9 10                                                                              11                                                                              1  9                __________________________________________________________________________    POSTEMERGENCE                                                                 Barley     10  9                                                                              10                                                                              10                                                                              10 10                                                                               8                                                                               5                                                                              10                                                                              10 10                                                                               8                                                                               8                                                                               4                                                                               9                                                                              10                                                                              10                                                                              7  7                                                                              0  9                                                                               8                                                                               9 0                Blackgrass 10 10                                                                              10                                                                              10                                                                               9  9                                                                              10                                                                               7                                                                              10                                                                               9  9                                                                               8                                                                              10                                                                               5                                                                               9                                                                               9                                                                               9                                                                              6       39                                                                             7                                                                               7 0                Chickweed   7 10                                                                              10                                                                              10                                                                              10  6                                                                              10                                                                                7                                                                             10                                                                              10 10                                                                               3                                                                               9                                                                               3                                                                              10                                                                               9                                                                              10                                                                              0       08                                                                             8                                                                              10 0                Cocklebur  10 10                                                                              10                                                                              10                                                                              10  8                                                                              10                                                                              --                                                                              10                                                                              10 10                                                                               2                                                                               9                                                                              --                                                                              10                                                                              10                                                                              10                                                                              0       --                                                                            10                                                                            10                                                                               9 --               Corn       10  9                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                              10                                                                              10                                                                              10 10                                                                               8                                                                               8                                                                               0                                                                              10                                                                              10                                                                               9                                                                              8       08                                                                             9                                                                               9 0                Cotton      3 10                                                                              10                                                                              10                                                                              10  2                                                                               9                                                                              10                                                                              10                                                                              10  9                                                                               0                                                                               9                                                                               3                                                                               9                                                                               9                                                                               8                                                                              0       07                                                                             4                                                                               5 0                Crabgrass   9 10                                                                              10                                                                              10                                                                              10  8                                                                               7                                                                              10                                                                              10                                                                              10  9                                                                               3                                                                               7                                                                               3                                                                               9                                                                               9                                                                               6                                                                              3       05                                                                             7                                                                               4 0                Downy brome                                                                              10  9                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                               7                                                                              10                                                                               9 10                                                                              10                                                                               8                                                                               0                                                                               9                                                                               9                                                                              10                                                                              9       08                                                                             7                                                                               9 0                Giant foxtail                                                                            10  8                                                                               8                                                                               9                                                                              10 10                                                                               7                                                                              10                                                                               5                                                                               6 10                                                                               9                                                                               4                                                                               3                                                                               3                                                                               3                                                                              10                                                                              5       02                                                                             0                                                                               6 0                Green foxtail                                                                            10  9                                                                              10                                                                              10                                                                              10 10                                                                               8                                                                              10                                                                               5                                                                               8 10                                                                              10                                                                               6                                                                               0                                                                               3                                                                               3                                                                              10                                                                              7       02                                                                             0                                                                              10 0                Jimsonweed 10 10                                                                              10                                                                              10                                                                              10  9                                                                              10                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                              10                                                                               3                                                                              10                                                                              10                                                                              10                                                                              8       09                                                                            10                                                                            10                                                                               9 0                Johnsongrass                                                                             10  9                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                               9                                                                              10                                                                              10 10                                                                               9                                                                               8                                                                               0                                                                               9                                                                              10                                                                              10                                                                              5       08                                                                             7                                                                               8 0                Lambsquarters                                                                            10 10                                                                              10                                                                              10                                                                              10  7                                                                               8                                                                              10                                                                              10                                                                              10 10                                                                               5                                                                               8                                                                               7                                                                              10                                                                               9                                                                              10                                                                              2       37                                                                             5                                                                               8 0                Morningglory                                                                              7 10                                                                              10                                                                              10                                                                              10  4                                                                               9                                                                               9                                                                              10                                                                              10 10                                                                               0                                                                               9                                                                               6                                                                              10                                                                               9                                                                              10                                                                              0       49                                                                             9                                                                              10 3                Nutsedge    6 10                                                                              10                                                                              10                                                                              10  4                                                                               8                                                                              10                                                                               9                                                                               7  8                                                                               0                                                                               8                                                                               3                                                                               9                                                                               5                                                                               8                                                                              0       37                                                                             2                                                                               7 0                Rape       10 10                                                                              10                                                                              10                                                                              10 10                                                                              10                                                                               9                                                                               9                                                                              10 10                                                                               5                                                                               9                                                                               9                                                                               9                                                                              10                                                                              10                                                                              0       38                                                                            10                                                                              10 3                Rice Dry Seed                                                                            10  9                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                               6                                                                              10                                                                              10 10                                                                              10                                                                               8                                                                               0                                                                              10                                                                              10                                                                              10                                                                              8       08                                                                             9                                                                               9 0                Sicklepod   8 10                                                                              10                                                                              10                                                                              10  8                                                                               8                                                                               8                                                                               8                                                                              10 10                                                                               0                                                                               8                                                                               0                                                                               8                                                                              10                                                                               9                                                                              0       04                                                                             4                                                                               4 0                Soybean     9  9                                                                              10                                                                              10                                                                              10  7                                                                               8                                                                               8                                                                               9                                                                               8 10                                                                               1                                                                               8                                                                               0                                                                               8                                                                               7                                                                              10                                                                              0       03                                                                             7                                                                               9 0                Sugar beet 10 10                                                                              10                                                                              10                                                                              10 10                                                                              10                                                                              10                                                                              10                                                                               9 10                                                                               9                                                                              10                                                                              10                                                                              10                                                                               8                                                                              10                                                                              4       79                                                                            10                                                                             3                                                                              10 4                Teaweed     6  8                                                                              9 10                                                                              10  5                                                                               8                                                                               8                                                                               8                                                                               9 10                                                                               3                                                                               3                                                                               0                                                                               8                                                                               7                                                                              10                                                                              3       03                                                                             3                                                                              10 0                Velvetleaf  4 10                                                                              10                                                                              10                                                                              10  0                                                                              10                                                                              10                                                                              10                                                                              10 10                                                                               0                                                                              10                                                                               3                                                                              10                                                                              10                                                                               9                                                                              0       10                                                                            0                                                                              3                                                                               9 0                Wheat      10  9                                                                               9                                                                              10                                                                               9  9                                                                               8                                                                               6                                                                               9                                                                               9  9                                                                               8                                                                               8                                                                               4                                                                               9                                                                               8                                                                               6                                                                              6       08                                                                             7                                                                               5 0                Wild buckwheat                                                                           10 10                                                                              10                                                                              --                                                                              10  5                                                                              10                                                                               8                                                                              10                                                                               9 10                                                                               0                                                                                9                                                                              4                                                                               5                                                                               7                                                                              10                                                                              0       08                                                                            --                                                                             3                                                                              10 0                Wild oat   10  8                                                                              10                                                                              10                                                                              10 10                                                                               8                                                                               7                                                                               9                                                                              10 10                                                                              10                                                                               7                                                                               2                                                                               9                                                                               9                                                                              10                                                                              8       05                                                                             8                                                                               9 0                Barnyardgrass                                                                            10  9                                                                              10                                                                              10                                                                              10 10                                                                               9                                                                              10                                                                              10                                                                              10 10                                                                               8                                                                               9                                                                               3                                                                               9                                                                              10                                                                               5                                                                              4       09                                                                             9                                                                               4 0                PREEMERGENCE                                                                  Barley     10  7                                                                               9                                                                               9                                                                              10  9                                                                               4                                                                               0                                                                               7                                                                               3 10                                                                               4                                                                               2                                                                               0                                                                               3                                                                               0                                                                               5                                                                              0  0                                                                              0  0                                                                               0                                                                               2 0                Blackgrass  8  9                                                                               9                                                                               9                                                                               9  6                                                                               9                                                                               5                                                                               8                                                                               7  8                                                                               5                                                                               8                                                                               0                                                                               8                                                                               4                                                                               6                                                                              3       04                                                                             0                                                                               0 0                Chickweed   5  8                                                                               9                                                                               9                                                                              10  0                                                                               7                                                                               8                                                                               8                                                                               8 10                                                                               0                                                                               5                                                                               7                                                                               7                                                                               7                                                                               9                                                                              0       73                                                                             3                                                                               7 6                Cocklebur   8  5                                                                               9                                                                              --                                                                              10 --                                                                              --                                                                               5                                                                               8                                                                               3  8                                                                               3                                                                               2                                                                              --                                                                               3                                                                               0                                                                               7                                                                              0       00                                                                            --                                                                             0                                                                               0 0                Corn       10  9                                                                              10                                                                              10                                                                              10  7                                                                               6                                                                               3                                                                               9                                                                               4  8                                                                               4                                                                               4                                                                               0                                                                               8                                                                               4                                                                               3                                                                              0       00                                                                             2                                                                               2 0                Cotton      8  9                                                                               9                                                                              10                                                                               9  5                                                                               4                                                                               3                                                                               8                                                                               8  8                                                                               0                                                                               2                                                                               0                                                                               6                                                                               3                                                                               5                                                                              0       00                                                                             0                                                                               0 0                Crabgrass   9 10                                                                              10                                                                              10                                                                              10  3                                                                               9                                                                              10                                                                              10                                                                              10 10                                                                               2                                                                               9                                                                              10                                                                               9                                                                               8                                                                               6                                                                              0       43                                                                             3                                                                               4 3                Downy brome                                                                              10 10                                                                              10                                                                               9                                                                              10 10                                                                               7                                                                               2                                                                              10                                                                               9 10                                                                               6                                                                               5                                                                               0                                                                               7                                                                               3                                                                               8                                                                              0       03                                                                             0                                                                               3 0                Giant foxtail                                                                            10  8                                                                               5                                                                               8                                                                              10  6                                                                               5                                                                               2                                                                               3                                                                               5  9                                                                               2                                                                               3                                                                               0                                                                               2                                                                               3                                                                               8                                                                              0       00                                                                             0                                                                               3 0                Green foxtail                                                                            10 10                                                                               8                                                                               9                                                                              10  9                                                                               9                                                                               5                                                                               5                                                                               5  9                                                                               3                                                                               5                                                                               2                                                                               3                                                                               3                                                                               7                                                                              0       03                                                                             0                                                                               3 0                Jimsonweed  9  9                                                                               9                                                                               9                                                                              10  9                                                                               3                                                                               0                                                                               9                                                                               9 10                                                                               8                                                                               0                                                                               0                                                                               5                                                                               3                                                                               9                                                                              6       00                                                                             0                                                                               4 0                Johnsongrass                                                                             10   9                                                                              9                                                                               9                                                                              10 10                                                                               7                                                                               3                                                                               8                                                                               3 10                                                                               5                                                                               3                                                                               2                                                                               7                                                                               0                                                                               9                                                                              0       00                                                                             0                                                                               5 0                Lambsquarters                                                                            10  9                                                                              10                                                                               9                                                                              10  8                                                                               9                                                                               9                                                                              10                                                                               8 10                                                                              --                                                                               8                                                                               8                                                                               9                                                                               5                                                                              10                                                                              --      05                                                                             0                                                                               0 0                Morningglory                                                                              8  9                                                                               9                                                                               9                                                                              10  8                                                                               8                                                                               0                                                                               9                                                                               8  9                                                                               3                                                                               4                                                                               0                                                                               8                                                                               3                                                                               8                                                                              3       00                                                                             0                                                                               6 0                Nutsedge    8  8                                                                               9                                                                               5                                                                              10  6                                                                               8                                                                               0                                                                               3                                                                               5 10                                                                               5                                                                               3                                                                               0                                                                               0                                                                               2                                                                               9                                                                              0       00                                                                             0                                                                               4 --               Rape        7  9                                                                              10                                                                               8                                                                              10  0                                                                               5                                                                               8                                                                              10                                                                               7  4                                                                               0                                                                               3                                                                               0                                                                               5                                                                               3                                                                               2                                                                              0       00                                                                             0                                                                               0 0                Rice Dry Seed                                                                            10  9                                                                              10                                                                              10                                                                               9  8                                                                               5                                                                               4                                                                              10                                                                              10  9                                                                               5                                                                               4                                                                               4                                                                               6                                                                               8                                                                               6                                                                              1       32                                                                             3                                                                               3 0                Sicklepod   8  8                                                                               9                                                                               5                                                                               9  8                                                                               7                                                                               3                                                                               5                                                                              --  9                                                                               3                                                                               3                                                                               0                                                                               5                                                                               2                                                                               7                                                                              --      --                                                                             0                                                                               5 --               Soybean     6  8                                                                               8                                                                               8                                                                              10  0                                                                               3                                                                               4                                                                               4                                                                               4  5                                                                              0  0                                                                               3                                                                               2                                                                               2                                                                               3                                                                              0       00                                                                             0                                                                               0 0                Sugar beet 10  9                                                                              10                                                                               5                                                                              10  9                                                                               9                                                                               3                                                                               9                                                                               5 10                                                                               6                                                                               3                                                                               0                                                                               7                                                                               5                                                                              10                                                                              0       00                                                                             5                                                                               9 0                Teaweed     9  9                                                                               9                                                                               9                                                                               9  9                                                                               9                                                                               7                                                                               9                                                                               7  9                                                                               9                                                                               5                                                                               0                                                                               9                                                                               3                                                                               9                                                                              9       --                                                                             0                                                                               8 --               Velvetleaf  2  9                                                                               9                                                                               9                                                                               9  1                                                                               8                                                                               8                                                                               8                                                                               9  9                                                                               0                                                                               5                                                                               6                                                                               8                                                                               8                                                                               4                                                                              0       45                                                                             3                                                                               0 4                Wheat      10  7                                                                               9                                                                               9                                                                               9 10                                                                               4                                                                               0                                                                               7                                                                               5  4                                                                               4                                                                               2                                                                               0                                                                               3                                                                               3                                                                               2                                                                              --      00                                                                             0                                                                               0 0                Wild buckwheat                                                                            5 10                                                                               9                                                                               9                                                                              10  3                                                                               9                                                                              --                                                                               9                                                                               9  9                                                                               0                                                                               5                                                                              --                                                                               8                                                                               7                                                                               8                                                                              0       --                                                                             2                                                                               5 --               Wild oat    9  7                                                                               8                                                                               5                                                                              10  4                                                                               5                                                                               0                                                                              10                                                                               8  9                                                                                3                                                                              4                                                                               0                                                                               3                                                                               3                                                                               5                                                                              0       00                                                                             2                                                                               3 0                Barnyardgrass                                                                             9 10                                                                              10                                                                              10                                                                              10  6                                                                               5                                                                               5                                                                              10                                                                               8  7                                                                               0                                                                               4                                                                               2                                                                               5                                                                               5                                                                               2                                                                              0       00                                                                             0                                                                               0 0                __________________________________________________________________________

TEST D

The compounds evaluated in this test were formulated in a non-phytoxicsolvent and applied to the soil surface before plant seedlings emerged(preemergence application), to water that covered the soil surface(paddy application), and to plants that were in the one-to-four leafstage (postemergence application). A sandy loam soil was used for thepreemergence and postemergence tests, while a silt loam soil was used inthe paddy test. Water depth was approximately 2.5 cm for the paddy testand was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted ofbarley (Hordeum vulgare), bedstraw (Galium aparine), blackgrass(Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays),cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downybrome (Bromus tectorum), giant foxtail (Setaria faberii), lambsquarters(Chenopodium album), morningglory (Ipomoea hederacea), pigweed(Amaranthusretroflexus), rape (Brassica napus), ryegrass (Loliummultiflorum), sorghum (Sorghum bicolor), soybean (Glycine max),speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf(Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat(Polygonum convolvulus), and wild oat (Avena fatua). All plant specieswere planted one day before application of the compound for thepreemergence portion of this test. Plantings of these species wereadjusted to produce plants of appropriate size for the postemergenceportion of the test. Plant species in the paddy test consisted ofbarnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), andumbrella sedge (Cyperus difformis).

All plant species were grown using normal greenhouse practices. Visualevaluations of injury expressed on treated plants, when compared tountreated controls, were recorded approximately fourteen to twenty-onedays after application of the test compound. Plant response ratings,summarized in Table D, were recorded on a 0 to 10 scale where 0 is noinjury and 10 is complete control. A dash (-) response means no testresult.

                                      TABLE D                                     __________________________________________________________________________    POSTEMERGENCE                                                                           Rate (250 g/ha)                                                                       Rate (125 g/ha)                                                                       Rate (62 g/ha)                                                COMPOUND                                                                              COMPOUND                                                                              COMPOUND                                                      5       42      3 4 5 6 14                                                                              18                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                __________________________________________________________________________    Barley Igri                                                                             8       10      9 10                                                                              7 10                                                                              10                                                                              10                                                                              6 7 6 6 10                                                                              9 10                                                                              10                                                                              6 6    0                                                                        6                     Bedstraw  10      10      9 10                                                                              8 10                                                                              10                                                                              10                                                                              7 10                                                                              10                                                                              7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Blackgrass                                                                              7       10      7 8 6 10                                                                              10                                                                              10                                                                              9 8 7 8 10                                                                              9 10                                                                              10                                                                              10                                                                              10   7                                                                        10                    Chickweed 9       10      10                                                                              10                                                                              6 10                                                                              10                                                                              10                                                                              3 10                                                                              --                                                                              --                                                                              10                                                                              10                                                                              10                                                                              10                                                                              --                                                                              --   --                                                                       --                    Corn      10      10      10                                                                              10                                                                              7 10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Cotton    0       9       7 8 0 7 9 7 3 7 8 0 8 9 9 10                                                                              10                                                                              10   9                                                                        10                    Crabgrass 9       8       9 10                                                                              6 9 9 9 5 9 9 7 7 10                                                                              10                                                                              10                                                                              10                                                                              9    7                                                                        8                     Downy brome                                                                             10      10      8 9 9 10                                                                              10                                                                              10                                                                              9 8 7 8 10                                                                              9 10                                                                              10                                                                              7 7    4                                                                        10                    Giant foxtail                                                                           10      8       10                                                                              10                                                                              8 10                                                                              10                                                                              10                                                                              7 10                                                                              10                                                                              10                                                                              7 10                                                                              7 10                                                                              10                                                                              10   10                                                                       10                    Lambsquarters                                                                           10      10      10                                                                              10                                                                              8 10                                                                              10                                                                              10                                                                              4 10                                                                              10                                                                              6 10                                                                              10                                                                              10                                                                              10                                                                              9 10   8                                                                        10                    Morningglory                                                                            2       8       9 10                                                                              0 8 9 10                                                                              5 10                                                                              9 5 8 10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Pigweed   10      10      10                                                                              10                                                                              9 9 9 10                                                                              9 10                                                                              9 9 10                                                                              10                                                                              10                                                                              10                                                                              9 10   10                                                                       10                    Rape      6       10      10                                                                              10                                                                              2 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              8 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Ryegrass  10      8       8 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              6 10                                                                              8 9 10                                                                              10                                                                              7 8    6                                                                        8                     Sorghum   9       10      10                                                                              10                                                                              8 10                                                                              10                                                                              10                                                                              7 10                                                                              9 9 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Soybean   4       10      9 10                                                                              3 10                                                                              9 10                                                                              8 10                                                                              8 8 10                                                                              10                                                                              10                                                                              10                                                                              9 10   9                                                                        10                    Speedwell 0       6       8 8 0 10                                                                              6 6 0 9 5 8 6 8 6 6 10                                                                              9    9                                                                        10                    Sugar beet                                                                              9       10      8 10                                                                              6 10                                                                              10                                                                              10                                                                              7 10                                                                              7 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Velvetleaf                                                                              3       9       9 9 0 10                                                                              9 10                                                                              7 9 3 0 8 10                                                                              9 10                                                                              9 10   10                                                                       9                     Wheat     7       10      7 7 6 10                                                                              10                                                                              10                                                                              10                                                                              7 6 6 10                                                                              9 10                                                                              10                                                                              6 7    3                                                                        6                     Wild buckwheat                                                                          6       10      8 10                                                                              6 10                                                                              10                                                                              8 9 10                                                                              8 8 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   9                                                                        10                    Wild oat  8       10      7 8 8 9 10                                                                              10                                                                              9 6 6 7 10                                                                              9 10                                                                              10                                                                              6 6    0                                                                        6                     Barnyardgrass                                                                           3       8       5 7 0 9 9 6 2 9 9 6 5 9 6 9 2 8    6                                                                        5                     Rice Japonica                                                                           8       8       8 8 3 8 9 7 4 9 8 4 7 8 8 9 7 9    9                                                                        5                     Umbrella sedge    7       3 9 --                                                                              0 10                                                                              9 7 8 9 2 6 9 8 9 6 6    0                                                                        6                     __________________________________________________________________________    POSTEMERGENCE                                                                          Rate (31 g/ha)                Rate (16 g/ha)                                  COMPOUND                      COMPOUND                                        14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              3 4 5 6 14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42               __________________________________________________________________________    Barley Igri                                                                            10                                                                              10                                                                              10                                                                              5 7 5 6 10                                                                              9 10                                                                              10                                                                              5 6 0 5 6 8 6       9                                                                             10                                                                            10                                                                            10                                                                              3 7 5 5  10              Bedstraw 10                                                                              10                                                                              10                                                                              7 10                                                                              8 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              8 9 5       10                                                                            7                                                                             5                                                                             10                                                                              4 10                                                                              7 7  10              Blackgrass                                                                             10                                                                              10                                                                              10                                                                              5 8 7 7 8 9 10                                                                              10                                                                              10                                                                              10                                                                              7 8 6 7 3       9                                                                             10                                                                            10                                                                            10                                                                              3 8 7 6  8               Chickweed                                                                              10                                                                              10                                                                              10                                                                              0 10                                                                              --                                                                              --                                                                              10                                                                              10                                                                              10                                                                              10                                                                              --                                                                              --                                                                              --                                                                              --                                                                              10                                                                              10                                                                              3       10                                                                            9                                                                             8                                                                             10                                                                              0 10                                                                              --                                                                              -- 8               Corn     10                                                                              10                                                                              10                                                                              7 10                                                                              9 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              4       10                                                                            10                                                                            10                                                                            10                                                                              6 10                                                                              9 9  10              Cotton   8 7 9 2 7 7 0 7 8 9 10                                                                              9 10                                                                              9 10                                                                              6 7 0       7                                                                             7                                                                             6                                                                             8 2 6 7 0  7               Crabgrass                                                                              8 8 9 3 9 9 6 6 10                                                                              8 10                                                                              9 8 5 4 9 9 3       8                                                                             8                                                                             7                                                                             8 2 8 8 4  5               Downy brome                                                                            10                                                                              10                                                                              10                                                                              9 8 7 7 10                                                                              9 10                                                                              10                                                                              7 6 3 8 7 8 8       9                                                                             9                                                                             10                                                                            10                                                                              6 7 7 6  9               Giant foxtail                                                                          10                                                                              10                                                                              10                                                                              7 10                                                                              10                                                                              9 7 10                                                                              7 10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              7       10                                                                            10                                                                            8                                                                             10                                                                              5 10                                                                              10                                                                              9  7               Lambsquarters                                                                          10                                                                              10                                                                              10                                                                              4 10                                                                              10                                                                              6 10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              6 9 9 10                                                                              6       10                                                                            10                                                                            10                                                                            10                                                                              3 10                                                                              10                                                                              4  10              Morningglory                                                                           9 10                                                                              10                                                                              4 10                                                                              8 4 8 10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              10                                                                              8 10                                                                              0       7                                                                             9                                                                             10                                                                            10                                                                              3 10                                                                              7 4  7               Pigweed  9 9 10                                                                              7 10                                                                              9 8 10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9       8                                                                             7                                                                             8                                                                             10                                                                              6 8 8 8  8               Rape     10                                                                              --                                                                              10                                                                              9 10                                                                              8 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              7 10                                                                              0       10                                                                            10                                                                            10                                                                            10                                                                              7 10                                                                              7 4  10              Ryegrass 9 10                                                                              10                                                                              9 10                                                                              6 8 8 6 10                                                                              10                                                                              7 7 5 7 6 7 6       8                                                                             7                                                                             10                                                                            10                                                                              8 8 6 6  5               Sorghum  9 10                                                                              10                                                                              6 10                                                                              9 9 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              6       10                                                                            9                                                                             10                                                                            10                                                                              6 10                                                                              9 8  8               Soybean  9 10                                                                              10                                                                              7 10                                                                              8 6 9 10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              8 9 0       10                                                                            9                                                                             10                                                                            10                                                                              6 8 7 5  9               Speedwell                                                                              6 6 0 0 8 3 7 3 3 --                                                                              5 9 7 7 10                                                                              8 8 0       10                                                                            5                                                                             6                                                                             0 0 8 0 5  3               Sugar beet                                                                             10                                                                              10                                                                              10                                                                              7 10                                                                              7 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              8 10                                                                              3       10                                                                            10                                                                            10                                                                            10                                                                              6 10                                                                              7 5  10              Velvetleaf                                                                             9 9 10                                                                              3 8 3 0 7 8 8 10                                                                              9 10                                                                              10                                                                              9 8 9 0       8                                                                             9                                                                             8                                                                             9 3 7 2 0  6               Wheat    10                                                                              10                                                                              10                                                                              8 6 6 6 10                                                                              9 9 10                                                                              6 5 3 6 6 6 6       4                                                                             10                                                                            10                                                                            10                                                                              7 6 6 5  9               Wild buckwheat                                                                         10                                                                              8 10                                                                              7 10                                                                              7 7 10                                                                              9 10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              7 9 0       10                                                                            9                                                                             7                                                                             10                                                                              6 10                                                                              7 6  9               Wild oat 10                                                                              10                                                                              10                                                                              9 4 5 7 10                                                                              9 10                                                                              10                                                                              4 6 0 5 6 7 6       5                                                                             9                                                                             10                                                                            10                                                                              5 4 5 6  9               Barnyardgrass                                                                          2 4 1 2 9 8 1 4 8 4 9 1 8 0 2 0 6 0       6                                                                             2                                                                             0                                                                             1 0 7 8 0  2               Rice Japonica                                                                          8 4 7 4 9 8 1 4 8 5 9 6 7 5 1 7 7 0       7                                                                             6                                                                             0                                                                             5 3 6 8 0  0               Umbrella sedge                                                                         9 9 9 4 8 9 0 5 9 7 8 4 6 0 4 0 0 --      0                                                                             8                                                                             8                                                                             9 2 7 8 0  0               __________________________________________________________________________    POSTEMERGENCE                                                                          Rate (16 g/ha)                                                                              Rate (8 g/ha)                 Rate (4 g/ha)                     COMPOUND      COMPOUND                      COMPOUND                          47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              3 4 5 6 14               __________________________________________________________________________    Barley Igri                                                                            9 10                                                                              10                                                                              3 5 0 4 9 10                                                                              10                                                                              0 6 5 4 7 7 9 10      3                                                                             5                                                                             0                                                                             3 5 6 5 6  6               Bedstraw 10                                                                              10                                                                              10                                                                              8 10                                                                              10                                                                              8 6 5 10                                                                              4 7 7 6 5 9 10                                                                              10      7                                                                             8                                                                             10                                                                            8 7 9 3 10 4               Blackgrass                                                                             9 10                                                                              10                                                                              10                                                                              9 6 7 10                                                                              10                                                                              9 3 7 6 6 5 8 9 10      8                                                                             7                                                                             5                                                                             7 3 7 0 8  10              Chickweed                                                                              10                                                                              10                                                                              10                                                                              --                                                                              --                                                                              --                                                                              --                                                                              8 7 10                                                                              0 9 --                                                                              --                                                                              8 10                                                                              10                                                                              10      --                                                                            --                                                                            --                                                                            --                                                                              6 10                                                                              0 10 8               Corn     10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              10                                                                              6 9 9 9 10                                                                              10                                                                              10                                                                              10      10                                                                            10                                                                            9                                                                             9 9 9 2 10 9               Cotton   7 7 10                                                                              8 10                                                                              8 10                                                                              5 5 6 0 4 4 0 6 7 6 9       6                                                                             10                                                                            7                                                                             9 2 5 0 6  5               Crabgrass                                                                              8 7 8 9 7 4 3 7 7 7 0 7 8 3 4 6 6 7       8                                                                             6                                                                             4                                                                             3 7 8 0 8  5               Downy brome                                                                            8 10                                                                              10                                                                              6 6 2 7 5 9 10                                                                              4 6 6 6 6 7 9 10      6                                                                             5                                                                             0                                                                             6 5 7 3 5  4               Giant foxtail                                                                          10                                                                              7 10                                                                              10                                                                              10                                                                              6 10                                                                              9 7 10                                                                              5 8 9 8 6 8 7 9       9                                                                             9                                                                             6                                                                             10                                                                              6 8 3 8  7               Lambsquarters                                                                          10                                                                              10                                                                              10                                                                              7 10                                                                              6 7 10                                                                              10                                                                              10                                                                              3 10                                                                              9 2 9 9 10                                                                              10      6                                                                             10                                                                            6                                                                             6 9 10                                                                              3 10 9               Morningglory                                                                           10                                                                              8 10                                                                              9 9 9 10                                                                              7 8 10                                                                              2 7 7 2 7 10                                                                              7 10      8                                                                             7                                                                             9                                                                             9 8 9 0 7  5               Pigweed  10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              4 6 7 3 7 8 7 8 8 10                                                                              10      9                                                                             10                                                                            9                                                                             10                                                                              9 9 5 8  3               Rape     10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              4 10                                                                              7 4 10                                                                              9 10                                                                              10      10                                                                            10                                                                            10                                                                            10                                                                              6 8 0 9  9               Ryegrass 4 10                                                                              10                                                                              7 6 4 6 5 8 7 4 7 5 6 4 2 7 10      6                                                                             4                                                                             3                                                                             6 4 5 4 6  3               Sorghum  10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              10                                                                              5 10                                                                              9 8 7 10                                                                              10                                                                              10      9                                                                             10                                                                            9                                                                             10                                                                              8 10                                                                              6 8  8               Soybean  10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              9 9 10                                                                              3 7 7 5 7 10                                                                              9 10      9                                                                             9                                                                             9                                                                             9 8 9 0 6  7               Speedwell                                                                              2 6 --                                                                              8 6 7 9 4 5 0 0 7 0 5 0 1 6 --      7                                                                             6                                                                             6                                                                             7 7 8 0 7  0               Sugar beet                                                                             10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              8 10                                                                              10                                                                              9 5 10                                                                              3 5 8 10                                                                              10                                                                              10      10                                                                            10                                                                            10                                                                            8 8 10                                                                              0 10 9               Velvetleaf                                                                             7 7 10                                                                              8 9 8 9 8 7 9 2 5 2 0 6 7 7 10      7                                                                             9                                                                             7                                                                             9 7 7 0 6  6               Wheat    8 8 10                                                                              5 4 0 6 8 9 10                                                                              4 6 5 3 0 5 8 9       5                                                                             3                                                                             0                                                                             6 5 6 5 0  7               Wild buckwheat                                                                         9 10                                                                              10                                                                              8 10                                                                              9 10                                                                              9 5 7 3 7 7 2 9 9 9 10      7                                                                             10                                                                            9                                                                             7 5 9 0 9  6               Wild oat 9 10                                                                              10                                                                              3 5 0 4 7 10                                                                              10                                                                              4 0 4 5 5 8 9 9       0                                                                             4                                                                             0                                                                             3 5 6 4 0  7               Barnyardgrass                                                                          8 4 9 0 0 0 0 0 0 1 0 5 5 0 0 8 0 6       0                                                                             0                                                                             0                                                                             0 0 5 0 0  0               Rice Japonica                                                                          8 3 9 5 4 1 1 2 0 0 2 1 6 0 0 6 0 8       2                                                                             0                                                                             0                                                                             0 0 3 0 0  2               Umbrella sedge                                                                         9 3 8 0 3 0 0 3 6 7 0 6 8 0 0 7 1 7       0                                                                             2                                                                             0                                                                             0 0 0 --                                                                              0  0               __________________________________________________________________________    POSTEMERGENCE                                                                                              Rate (4 g/ha)             Rate (2 g/ha)                                       COMPOUND                  COMPOUND                                            18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              19                     __________________________________________________________________________                        Barley Igri                                                                            9 10                                                                              0 5 5 4 5 9 9 0 4 0 2 9                                          Bedstraw 4 9 0 5 6 0 8 9 10                                                                              5 8 8 8 5                                          Blackgrass                                                                             10                                                                              9 2 7 6 6 6 9 10                                                                              7 7 4 6 8                                          Chickweed                                                                              6 10                                                                              0 8 --                                                                              --                                                                              9 10                                                                              10                                                                              --                                                                              --                                                                              --                                                                              --                                                                              9                                          Corn     10                                                                              10                                                                              6 7 8 8 10                                                                              10                                                                              10                                                                              9 10                                                                              9 9 10                                         Cotton   3 5 0 2 3 0 6 6 8 5 10                                                                              4 4 4                                          Crabgrass                                                                              6 6 0 6 7 0 5 5 6 7 5 3 2 6                                          Downy brome                                                                            8 9 0 5 6 6 4 8 10                                                                              5 4 0 5 8                                          Giant foxtail                                                                          6 7 5 8 9 6 6 6 8 7 9 5 9 7                                          Lambsquarters                                                                          9 10                                                                              0 10                                                                              8 2 9 10                                                                              --                                                                              5 10                                                                              6 5 10                                         Morningglory                                                                           6 10                                                                              0 7 7 0 10                                                                              6 10                                                                              6 5 7 9 9                                          Pigweed  4 6 0 6 7 7 8 10                                                                              10                                                                              8 10                                                                              9 9 6                                          Rape     8 7 2 7 6 0 9 9 10                                                                              8 10                                                                              10                                                                              10                                                                              6                                          Ryegrass 5 3 3 6 3 6 0 5 10                                                                              4 3 0 3 0                                          Sorghum  8 8 3 10                                                                              9 8 10                                                                              10                                                                              10                                                                              9 10                                                                              9 10                                                                              7                                          Soybean  7 10                                                                              0 6 7 3 10                                                                              8 9 8 9 9 9 10                                         Speedwell                                                                              4 0 0 5 0 3 0 5 0 5 3 6 6 0                                          Sugar beet                                                                             9 9 4 10                                                                              0 4 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              7 7                                          Velvetleaf                                                                             5 7 0 3 0 0 6 7 9 4 8 6 6 6                                          Wheat    9 9 3 6 4 0 4 8 9 3 3 0 5 9                                          Wild buckwheat                                                                         4 5 2 6 7 0 8 8 9 7 10                                                                              7 7 0                                          Wild oat 9 8 2 0 3 4 6 6 9 0 3 0 0 5                                          Barnyardgrass                                                                          0 0 0 5 3 0 6 0 4 0 0 0 0 0                                          Rice Japonica                                                                          0 0 1 1 0 0 4 0 8 0 0 0 0 0                                          Umbrella sedge                                                                         2 6 0 2 7 0 5 0 5 0 0 0 0 2                      __________________________________________________________________________    PREEMERGENCE                                                                            Rate (250 g/ha)                                                                       Rate (125 g/ha)                                                                       Rate (62 g/ha)                                                COMPOUND                                                                              COMPOUND                                                                              COMPOUND                                                      5       42      3 4 5 6 14                                                                              18                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                __________________________________________________________________________    Barley Igri                                                                             7       8       6 9 3 9 2 0 0 4 1 0 4 3 0 6 6 5    3                                                                        3                     Bedstraw  9       10      9 10                                                                              7 10                                                                              0 9 8 8 10                                                                              9 9 10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Blackgrass                                                                              7       9       5 10                                                                              3 8 7 10                                                                              0 10                                                                              10                                                                              10                                                                              7 --                                                                              10                                                                              10                                                                              9 9    9                                                                        10                    Chickweed 8       10      7 10                                                                              3 8 8 9 5 10                                                                              9 5 7 10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Corn      0       4       2 9 0 7 2 10                                                                              2 9 4 0 2 3 6 10                                                                              7 --   8                                                                        --                    Cotton    0       7       2 2 0 7 3 5 0 8 4 0 5 0 8 9 6 8    7                                                                        6                     Crabgrass 10      7       8 9 5 10                                                                              5 5 0 7 7 4 7 7 9 10                                                                              8 10   10                                                                       8                     Downy brome                                                                             8       10      9 10                                                                              6 8 5 0 2 8 9 0 9 8 8 9 9 3    4                                                                        10                    Giant foxtail                                                                           9       10      6 9 6 9 4 4 3 8 9 6 7 7 9 10                                                                              8 10   10                                                                       9                     Lambsquarters                                                                           10      10      10                                                                              10                                                                              9 10                                                                              7 10                                                                              9 10                                                                              10                                                                              9 10                                                                              6 10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Morningglory                                                                            6       6       9 9 4 8 0 3 0 8 3 2 4 4 9 10                                                                              10                                                                              4    6                                                                        8                     Pigweed   9       10      9 9 8 10                                                                              7 8 8 10                                                                              8 3 10                                                                              10                                                                              9 10                                                                              10                                                                              10   10                                                                       10                    Rape      0       10      10                                                                              10                                                                              0 9 7 6 6 9 5 0 10                                                                              7 10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Ryegrass  9       8       8 10                                                                              7 8 3 9 3 10                                                                              6 5 4 5 10                                                                              10                                                                              10                                                                              9    10                                                                       10                    Sorghum   9       10      9 9 3 10                                                                              4 5 0 9 9 6 10                                                                              9 7 10                                                                              10                                                                              10   10                                                                       10                    Soybean   2       7       4 4 2 6 2 4 0 --                                                                              4 0 6 6 6 10                                                                              8 8    7                                                                        6                     Speedwell 9       8       10                                                                              10                                                                              5 9 5 9 0 10                                                                              6 10                                                                              6 7 8 9 10                                                                              10   10                                                                       10                    Sugar beet                                                                              9       10      9 10                                                                              6 10                                                                              9 10                                                                              8 10                                                                              7 0 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10   10                                                                       10                    Velvetleaf                                                                              3       9       8 9 3 9 7 5 0 7 4 2 8 7 8 10                                                                              6 10   7                                                                        9                     Wheat     8       8       9 9 4 6 0 0 0 3 4 2 6 5 0 7 8 5    4                                                                        5                     Wild buckwheat                                                                          4       10      4 9 2 9 5 8 8 8 9 7 9 9 9 10                                                                              10                                                                              10   10                                                                       10                    Wild oat  8       4       4 6 3 0 4 4 0 0 0 3 4 7 4 6 2 5    0                                                                        0                     __________________________________________________________________________    PREEMERGENCE                                                                           Rate (31 g/ha)                Rate (16 g/ha)                                  COMPOUND                      COMPOUND                                        14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              3 4 5 6 14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42               __________________________________________________________________________    Barley Igri                                                                            0 0 0 0 3 0 0 3 2 0 4 4 3 0 0 3 0 0       4                                                                             0                                                                             0                                                                             0 0 2 0 0  3               Bedstraw 0 4 5 4 6 9 5 8 9 10                                                                              10                                                                              9 10                                                                              10                                                                              10                                                                              7 10                                                                              3       9                                                                             0                                                                             3                                                                             5 3 3 6 5  6               Blackgrass                                                                             4 8 9 0 10                                                                              9 7 6 9 10                                                                              9 9 8 9 10                                                                              4 6 2       6                                                                             2                                                                             6                                                                             6 0 8 8 7  5               Chickweed                                                                              7 7 10                                                                              2 10                                                                              8 3 6 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              4 10                                                                              0       8                                                                             5                                                                             7                                                                             10                                                                              0 8 7 3  5               Corn     0 4 2 0 7 3 0 0 2 6 10                                                                              7 3 6 4 2 4 0       6                                                                             0                                                                             2                                                                             2 0 2 2 0  0               Cotton   2 3 4 0 7 3 0 2 0 6 9 5 4 6 4 2 1 0       6                                                                             0                                                                             2                                                                             3 0 3 2 0  0               Crabgrass                                                                              2 4 5 0 6 6 3 3 5 8 10                                                                              6 10                                                                              10                                                                              6 7 5 0       6                                                                             0                                                                             2                                                                             5 0 5 4 0  0               Downy brome                                                                            3 0 9 2 6 3 0 8 6 6 8 9 3 2 8 9 10                                                                              3       5                                                                             2                                                                             0                                                                             7 0 3 0 0  5               Giant foxtail                                                                          2 2 8 0 8 6 2 6 6 5 9 6 10                                                                              8 6 4 6 0       6                                                                             0                                                                             0                                                                             7 0 6 5 0  3               Lambsquarters                                                                          7 10                                                                              10                                                                              2 10                                                                              9 9 10                                                                              6 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              2       10                                                                            2                                                                             5                                                                             10                                                                              0 9 5 0  9               Morningglory                                                                           0 2 0 0 7 2 0 2 3 9 10                                                                              9 4 6 8 5 5 3       6                                                                             0                                                                             0                                                                             0 0 7 0 0  0               Pigweed  2 7 9 2 9 6 3 10                                                                              10                                                                              9 9 10                                                                              10                                                                              10                                                                              10                                                                              9 9 6       10                                                                            0                                                                             7                                                                             9 0 8 5 0  10              Rape     3 6 6 6 8 2 0 6 6 9 10                                                                              10                                                                              7 10                                                                              10                                                                              5 5 0       8                                                                             0                                                                             6                                                                             6 6 8 0 0  5               Ryegrass 2 4 5 2 10                                                                              5 0 4 4 7 10                                                                              10                                                                              8 6 10                                                                              2 6 3       2                                                                             0                                                                             3                                                                             5 0 5 4 0  3               Sorghum  2 2 9 0 9 8 4 6 8 3 10                                                                              10                                                                              10                                                                              10                                                                              9 3 4 0       10                                                                            0                                                                             0                                                                             7 0 9 7 2  4               Soybean  0 2 3 0 4 3 0 3 6 5 10                                                                              7 8 6 6 0 1 2       3                                                                             0                                                                             0                                                                             0 0 4 2 0  0               Speedwell                                                                              5 9 5 0 9 5 6 6 --                                                                              8 9 10                                                                              9 10                                                                              10                                                                              9 9 3       8                                                                             2                                                                             8                                                                             3 0 8 5 -- 4               Sugar beet                                                                             5 9 10                                                                              5 10                                                                              6 0 7 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              8 8 5       10                                                                            5                                                                             9                                                                             7 5 9 4 0  6               Velvetleaf                                                                             5 2 3 0 6 3 0 6 6 7 10                                                                              6 10                                                                              7 6 5 5 0       8                                                                             4                                                                             0                                                                             2 0 5 2 0  6               Wheat    0 0 0 0 2 3 0 4 3 0 6 5 3 0 5 4 7 0       3                                                                             0                                                                             0                                                                             0 0 0 0 0  3               Wild buckwheat                                                                         2 6 8 6 7 8 6 8 6 8 10                                                                              10                                                                              10                                                                              10                                                                              9 3 3 --      6                                                                             0                                                                             3                                                                             3 2 6 5 4  6               Wild oat 2 2 3 0 0 0 0 2 0 3 5 0 3 0 0 3 2 0       0                                                                             0                                                                             1                                                                             0 0 0 0 0  1               __________________________________________________________________________    PREEMERGENCE                                                                           Rate (16 g/ha)                                                                              Rate (8 g/ha)                 Rate (4 g/ha)                     COMPOUND      COMPOUND                      COMPOUND                          47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              14                                                                              18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              42                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              3 4 5 6 14               __________________________________________________________________________    Barley Igri                                                                            0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0       0                                                                             0                                                                             0                                                                             0 2 0 0 2  0               Bedstraw 8 7 10                                                                              9 10                                                                              10                                                                              10                                                                              0 3 3 0 0 6 3 4 6 6 7       9                                                                             5                                                                             9                                                                             4 4 8 0 8  0               Blackgrass                                                                             9 7 8 9 7 9 6 0 5 6 0 6 6 3 0 5 6 8       9                                                                             7                                                                             8                                                                             6 0 0 0 2  0               Chickweed                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              5 5 10                                                                              0 7 7 3 3 5 9 10      10                                                                            10                                                                            10                                                                            10                                                                              2 8 0 2  2               Corn     0 2 10                                                                              6 --                                                                              3 4 0 0 0 0 2 --                                                                              0 0 0 0 7       3                                                                             --                                                                            0                                                                             --                                                                              0 1 0 3  0               Cotton   0 5 9 4 3 5 4 0 0 2 0 3 0 0 0 0 3 8       3                                                                             3                                                                             4                                                                             2 0 0 0 3  0               Crabgrass                                                                              4 4 9 5 10                                                                              7 5 0 0 2 0 3 0 0 0 3 3 9       4                                                                             7                                                                             6                                                                             4 6 4 0 4  0               Downy brome                                                                            3 3 7 5 0 0 2 0 0 0 0 2 0 0 3 0 0 4       0                                                                             0                                                                             0                                                                             0 3 3 0 2  0               Giant foxtail                                                                          3 4 8 4 10                                                                              7 5 0 0 3 0 5 4 0 0 0 2 8       3                                                                             4                                                                             6                                                                             4 3 4 0 0  0               Lambsquarters                                                                          0 9 10                                                                              9 10                                                                              9 7 0 4 5 0 9 --                                                                              0 --                                                                              0 7 10      3                                                                             10                                                                            9                                                                             3 5 9 0 10 0               Morningglory                                                                           2 7 8 8 4 6 6 0 0 0 0 5 0 0 0 0 5 7       7                                                                             3                                                                             6                                                                             5 1 2 0 4  0               Pigweed  8 8 8 8 10                                                                              10                                                                              10                                                                              0 5 7 0 8 4 0 7 7 8 8       8                                                                             9                                                                             10                                                                            10                                                                              8 7 3 8  0               Rape     5 6 10                                                                              6 5 3 10                                                                              0 6 6 6 7 0 0 3 4 5 9       6                                                                             5                                                                             2                                                                             5 3 0 0 7  0               Ryegrass 3 3 10                                                                              7 5 4 10                                                                              0 1 2 0 3 0 0 2 0 0 7       7                                                                             0                                                                             3                                                                             0 0 3 0 0  0               Sorghum  4 2 10                                                                              6 9 10                                                                              6 0 0 2 0 7 5 0 2 3 0 10      0                                                                             3                                                                             7                                                                             4 0 0 0 4  0               Soybean  3 3 10                                                                              5 6 5 6 0 0 0 0 2 0 0 0 2 2 9       4                                                                             4                                                                             4                                                                             3 0 0 2 2  0               Speedwell                                                                              4 7 8 10                                                                              9 10                                                                              10                                                                              0 6 3 0 8 5 3 3 0 7 7       10                                                                            9                                                                             9                                                                             9 --                                                                              7 3 7  0               Sugar beet                                                                             6 10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              10                                                                              3 4 --                                                                              4 9 4 0 5 5 9 10      9                                                                             9                                                                             10                                                                            9 3 8 0 2  0               Velvetleaf                                                                             6 4 10                                                                              4 6 5 5 4 0 0 0 3 0 0 0 4 4 8       3                                                                             6                                                                             3                                                                             4 3 4 0 4  0               Wheat    0 0 4 5 2 0 0 0 0 0 0 0 0 0 0 0 0 0       0                                                                             0                                                                             0                                                                             0 0 2 0 2  0               Wild buckwheat                                                                         6 7 9 8 9 10                                                                              8 0 3 3 0 6 5 0 2 0 7 9       8                                                                             8                                                                             8                                                                             8 2 0 0 5  0               Wild oat 0 0 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3       0                                                                             0                                                                             0                                                                             0 2 2 0 0  0               __________________________________________________________________________    PREEMERGENCE                                                                                               Rate (4 g/ha)             Rate (2 g/ha)                                       COMPOUND                  COMPOUND                                            18                                                                              19                                                                              21                                                                              22                                                                              29                                                                              30                                                                              47                                                                              51                                                                              52                                                                              55                                                                              56                                                                              58                                                                              59                                                                              19                     __________________________________________________________________________                        Barley Igri                                                                            0 0 0 0 0 0 0 0 0 0 0 0 0 0                                          Bedstraw 0 0 0 0 2 0 3 5 7 3 5 8 --                                                                              0                                          Blackgrass                                                                             3 4 0 3 5 3 4 5 8 8 4 4 5 3                                          Chickweed                                                                              3 9 0 6 3 --                                                                              0 8 10                                                                              10                                                                              10                                                                              9 9 3                                          Corn     0 0 0 0 2 0 0 0 4 0 0 0 --                                                                              0                                          Cotton   0 0 0 2 0 0 0 0 7 2 2 3 0 0                                          Crabgrass                                                                              0 0 0 0 0 0 0 0 8 3 5 3 3 0                                          Downy brome                                                                            0 0 0 0 0 0 0 0 3 0 0 0 0 0                                          Giant foxtail                                                                          0 2 0 2 3 0 0 0 6 2 0 4 3 0                                          Lambsquarters                                                                          0 0 0 7 0 --                                                                              0 4 7 0 10                                                                              --                                                                              3 0                                          Morningglory                                                                           0 0 0 3 0 0 0 3 7 5 3 5 4 0                                          Pigweed  4 7 0 7 3 0 7 5 8 8 9 8 8 3                                          Rape     6 6 6 5 0 0 3 3 8 6 3 0 4 6                                          Ryegrass 0 2 0 0 0 0 0 0 6 4 0 0 0 0                                          Sorghum  0 0 0 2 2 0 2 0 7 0 2 5 3 0                                          Soybean  0 0 0 0 0 0 0 0 7 3 4 3 2 0                                          Speedwell                                                                              4 2 0 7 0 2 0 5 7 8 5 9 8 0                                          Sugar beet                                                                             0 3 0 9 0 0 0 3 10                                                                              8 6 9 8 0                                          Velvetleaf                                                                             0 0 0 1 0 0 3 2 5 0 4 0 4 0                                          Wheat    0 0 0 0 0 0 0 0 0 0 0 0 0 0                                          Wild buckwheat                                                                         0 2 0 5 0 0 0 0 9 6 6 8 0 0                                          Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0                      __________________________________________________________________________

TEST E

Plastic pots were partially filled with silt loam soil. The soil wasthen flooded with water and Japonica rice (Oryza sativa) sprouted seedsand 1.5 leaf transplants were planted in the soil.

Seeds of barnyardgrass (Echinochloa crus-galli) were planted insaturated soil and plants grown to the 1 leaf and 2 leaf stages fortesting. At testing, the water level for all plantings was raised to 2cm above the soil surface. Chemical treatments were formulated in anon-phytotoxic solvent and applied directly to the paddy water.

Treated plants and controls were maintained in a greenhouse forapproximately 21 days, after which all species were compared to controlsand visually evaluated. Plant response ratings, summarize in Table E arereported on a 0 to 10 scale where 0 is no effect and 10 is completecontrol. A dash (-) response means no test result.

                  TABLE E                                                         ______________________________________                                                 COMPOUND                                                                      Rate   Rate    Rate     Rate  Rate                                            (500   (250    (100     (40   (16                                             g/ha)  g/ha)   g/ha)    g/ha) g/ha)                                           6      6       6        6     6                                      ______________________________________                                        Flood                                                                         1-LF B.Y. Grass                                                                          10       10      9      4     4                                    2-LF B.Y. Grass                                                                          7        6       3      3     8                                    Jap Direct Seed                                                                          9        9       9      5     3                                    Jap Rice Eff                                                                             9        8       8      6     4                                    ______________________________________                                          TEST G

Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa),barnyardgrass (Echinochloa crus-galli), bermudagrass (Cynodon dactylon),broadleaf signalgrass (Brachiaria plantaginea), common ragweed (Ambrosiaelatior), field bindweed (Convolvulus spp.), guineagrass (Panicummaximum), johnsongrass (Sorghum halepense), Kentucky bluegrass (Poapratensis), large crabgrass (Digitaria sanguinalis), P. J. legume(Pueraria javanica), pitted morningglory (Ipomoea lacunosa), purplenutsedge (Cyperus rotundus), smooth crabgrass (Digitaria ischaemum),purslane (Portulaca oleracea), TX panicum (Panicum Texas), and yellownutsedge (Cyperus esculentus) were planted into greenhouse potscontaining greenhouse planting medium. Each pot contained only one plantspecies. The test compound was dissolved in a non-phytotoxic solvent andapplied preemergence and/or postemergence to the plants. Preemergenceapplications were made within one day of planting the seeds or plantparts. Postemergence applications were applied when the plants were inthe two to four leaf stage (three to twenty cm).

Kentucky bluegrass was treated postemergence only. Test chemicals weredissolved in a non-phytotoxic solvent and applied preemergence andpostemergence to the plants. Untreated control plants and treated plantswere placed in the greenhouse and visually evaluated for injury at 13 to21 days after herbicide application. Plant response ratings, summarizedin Table G, are based on a 0 to 10 scale where 0 is no injury and 10 iscomplete control.

                  TABLE G                                                         ______________________________________                                                       COMPOUND                                                       ______________________________________                                        Rate (64 g/ha)   4                                                            POSTEMERGENCE                                                                 Alfalfa          10                                                           Barnyardgrass    9                                                            Bermudagrass     8                                                            Brdlf sgnalgrass 9                                                            Field bindweed   10                                                           Guineagrass      8                                                            Johnsongrass     10                                                           KY. Bluegrass    2                                                            Large crabgrass  10                                                           P.J. Legume      --                                                           Pitted mrnglory  8                                                            Purple nutsedge  10                                                           Purslane         7                                                            Ragweed          9                                                            Smooth crbgrass  9                                                            TX panicum       7                                                            Yellow nutsedge  5                                                            Rate (64 g/ha)   4                                                            PREEMERGENCE                                                                  Alfalfa          8                                                            Barnyardgrass    5                                                            Bermudagrass     9                                                            Brdlf sgnalgrass 10                                                           Field bindweed   8                                                            Guineagrass      9                                                            Johnsongrass     9                                                            KY. Bluegrass    --                                                           Large crabgrass  9                                                            P.J. Legume      8                                                            Pitted mrnglory  7                                                            Purple nutsedge  10                                                           Purslane         9                                                            Ragweed          9                                                            Smooth crbgrass  9                                                            TX panicum       10                                                           Yellow nutsedge  10                                                           Rate (32 g/ha)   4                                                            POSTEMERGENCE                                                                 Alfalfa          9                                                            Barnyardgrass    10                                                           Bermudagrass     5                                                            Brdlf sgnalgrass 10                                                           Field bindweed   8                                                            Guineagrass      8                                                            Johnsongrass     10                                                           KY. Bluegrass    2                                                            Large crabgrass  9                                                            P.J. Legume      --                                                           Pitted mrnglory  8                                                            Purple nutsedge  10                                                           Purslane         7                                                            Ragweed          10                                                           Smooth crbgrass  9                                                            TX panicum       7                                                            Yellow nutsedge  5                                                            Rate (32 g/ha)   4                                                            PREEMERGENCE                                                                  Alfalfa          8                                                            Barnyardgrass    1                                                            Bermudagrass     7                                                            Brdlf sgnalgrass 10                                                           Field bindweed   8                                                            Guineagrass      8                                                            Johnsongrass     8                                                            KY. Bluegrass    --                                                           Large crabgrass  5                                                            P.J. Legume      7                                                            Pitted mrnglory  3                                                            Purple nutsedge  10                                                           Purslane         9                                                            Ragweed          9                                                            Smooth crbgrass  9                                                            TX panicum       9                                                            Yellow nutsedge  9                                                            Rate (16 g/ha)   4                                                            POSTEMERGENCE                                                                 Alfalfa          7                                                            Barnyardgrass    8                                                            Bermudagrass     4                                                            Brdlf sgnalgrass 8                                                            Field bindweed   8                                                            Guineagrass      6                                                            Johnsongrass     9                                                            KY. Bluegrass    2                                                            Large crabgrass  8                                                            P.J. Legume      --                                                           Pitted mrnglory  6                                                            Purple nutsedge  6                                                            Purslane         4                                                            Ragweed          9                                                            Smooth crbgrass  8                                                            TX panicum       7                                                            Yellow nutsedge  5                                                            Rate (16 g/ha)   4                                                            PREEMERGENCE                                                                  Alfalfa          7                                                            Barnyardgrass    0                                                            Bermudagrass     3                                                            Brdlf sgnalgrass 9                                                            Field bindweed   8                                                            Guineagrass      6                                                            Johnsongrass     8                                                            KY. Bluegrass    --                                                           Large crabgrass  1                                                            P.J. Legume      7                                                            Pitted mrnglory  3                                                            Purple nutsedge  10                                                           Purslane         9                                                            Ragweed          9                                                            Smooth crbgrass  6                                                            TX panicum       8                                                            Yellow nutsedge  6                                                            Rate (4 g/ha)    4                                                            POSTEMERGENCE                                                                 Alfalfa          6                                                            Barnyardgrass    7                                                            Bermudagrass     3                                                            Brdlf sgnalgrass 8                                                            Field bindweed   8                                                            Guineagrass      6                                                            Johnsongrass     9                                                            KY. Bluegrass    2                                                            Large crabgrass  6                                                            P.J. Legume      --                                                           Pitted mrnglory  1                                                            Purple nutsedge  1                                                            Purslane         4                                                            Ragweed          9                                                            Smooth crbgrass  3                                                            TX panicum       7                                                            Yellow nutsedge  3                                                            Rate (4 g/ha)    4                                                            PREEMERGENCE                                                                  Alfalfa          6                                                            Barnyardgrass    0                                                            Bermudagrass     0                                                            Brdlf sgnalgrass 8                                                            Field bindweed   4                                                            Guineagrass      1                                                            Johnsongrass     2                                                            KY. Bluegrass    --                                                           Large crabgrass  0                                                            P.J. Legume      5                                                            Pitted mrnglory  2                                                            Purple nutsedge  5                                                            Purslane         9                                                            Ragweed          6                                                            Smooth crbgrass  2                                                            TX panicum       3                                                            Yellow nutsedge  0                                                            Rate (1 g/ha)    4                                                            POSTEMERGENCE                                                                 Alfalfa          3                                                            Barnyardgrass    1                                                            Bermudagrass     0                                                            Brdlf sgnalgrass 8                                                            Field bindweed   4                                                            Guineagrass      3                                                            Johnsongrass     9                                                            KY. Bluegrass    0                                                            Large crabgrass  4                                                            P.J. Legume      --                                                           Pitted mrnglory  0                                                            Purple nutsedge  --                                                           Purslane         1                                                            Ragweed          1                                                            Smooth crbgrass  0                                                            TX panicum       3                                                            Yellow nutsedge  2                                                            Rate (1 g/ha)    4                                                            PREEMERGENCE                                                                  Alfalfa          5                                                            Barnyardgrass    0                                                            Bermudagrass     0                                                            Brdlf sgnalgrass 0                                                            Field bindweed   1                                                            Guineagrass      0                                                            Johnsongrass     1                                                            KY. Bluegrass    --                                                           Large crabgrass  0                                                            P.J. Legume      5                                                            Pitted mrnglory  3                                                            Purple nutsedge  2                                                            Purslane         2                                                            Ragweed          1                                                            Smooth crbgrass  1                                                            TX panicum       0                                                            Yellow nutsedge  0                                                            ______________________________________                                    

TEST H

Seeds selected from crop and weed species consisting of blackgrass(Alopecurus myosuroides), catchweed bedstraw (Galium aparine), chickweed(Stellariamedia), lambsquarters (Chenopodium album), scentless chamomile(Matricaria inodora), speedwell (Veronica persica), sugar beet (Betavulgaris), field violet (Viola arvensis), wheat (Triticum aestivum),wild buckwheat (Polygonum convolvulus), wild oat (Avena fatua) wereplanted and treated preemergence with test chemicals dissolved in anon-phytotoxic solvent. Selected species from this list of crops andweeds were also treated with postermergence applications of testchemicals.

Plants ranged in height from two to twenty cm (two to three leaf stage)for postemergence treatments. Treated plants and controls weremaintained in a greenhouse for approximately 24 days, after which allspecies were compared to controls and visually evaluated.

The ratings, summarized in Table H, are based on a scale of 0 to 10where 0 is no effect and 10 is complete control. A dash (-) responsemeans no test.

                  TABLE H                                                         ______________________________________                                                       COMPOUND                                                       ______________________________________                                        Rate (64 g/ha)   11                                                           POSTEMERGENCE                                                                 Bedstraw         0                                                            Blackgrass       10                                                           Chickweed        5                                                            Field violet     7                                                            Lambsquarters    7                                                            Persian Speedwell                                                                              0                                                            Sntls Chamomile  5                                                            Sugar beet       4                                                            Wheat            8                                                            Wild buckwheat   7                                                            Wild oat         8                                                            Rate (32 g/ha)   11                                                           POSTEMERGENCE                                                                 Bedstraw         0                                                            Blackgrass       9                                                            Chickweed        4                                                            Field violet     4                                                            Lambsquarters    5                                                            Persian Speedwell                                                                              0                                                            Sntls Chamomile  3                                                            Sugar beet       3                                                            Wheat            8                                                            Wild buckwheat   7                                                            Wild oat         7                                                            Rate (16 g/ha)   11                                                           POSTEMERGENCE                                                                 Bedstraw         0                                                            Blackgrass       8                                                            Chickweed        4                                                            Field violet     3                                                            Lambsquarters    0                                                            Persian Speedwell                                                                              0                                                            Sntls Chamomile  0                                                            Sugar beet       2                                                            Wheat            6                                                            Wild buckwheat   2                                                            Wild oat         5                                                            Rate (8 g/ha)    11                                                           POSTEMERGENCE                                                                 Bedstraw         0                                                            Blackgrass       4                                                            Chickweed        0                                                            Field violet     0                                                            Lambsquarters    0                                                            Persian Speedwell                                                                              0                                                            Sntls Chamomile  0                                                            Sugar beet       0                                                            Wheat            5                                                            Wild buckwheat   0                                                            Wild oat         0                                                            ______________________________________                                    

What is claimed is:
 1. A compound of the formula ##STR60## wherein: L is##STR61## Q is O, S or NR⁸ ; Q¹ is O or NR⁸ ;Q² is O, S or NCH₃ ; R is Hor CH₃ ; R¹ is H, CH₃, Cl or Br; R² is H or CH₃ ; R³ is H, CH₃, F, Cl orBr; R⁴ is H, CH₃, F, Cl or Br; R⁵ is H or C₁ -C₃ alkyl; R⁶ is H, C₁ -C₃alkyl, C₁ -C₃ alkoxy, F, Cl, (C₁ -C₂ alkyl)carbonyloxy or C₁ -C₂alkylsulfonyloxy; R⁷ is CO₂ R⁹, CO₂ NR¹⁰ R¹¹, S(O)₂ NR¹⁰ R¹¹ or S(O)₂R¹² ; R⁸ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, allyl, propargyl or C₂-C₄ alkoxyalkyl; R⁹ is C₁ -C₄ alkyl; R¹⁰ is H or C₁ -C₂ alkyl; R¹¹ is Hor C₁ -C₂ alkyl; R¹² is C₁ -C₃ alkyl; w is CR¹³ or N; R¹³ is H, CH₃, Clor Br; m is 0, 1 or 2; n is 0 or 1; A is ##STR62## X is H, C₁ -C₄ alkyl,C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ haloalkyl, C₁ -C₄haloalkylthio, C₁ -C₄ alkylthio, halogen, C₂ -C₅ alkoxyalkyl, C₂ -C₅alkoxyalkoxy, amino, C₁ -C₃ alkylamino or di(C₁ -C₃ alkyl)amino; Y is H,C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄haloalkylthio, C₂ -C₅ alkoxyalkyl, C₂ -C₅ alkoxyalkoxy, amino, C₁ -C₃alkylamino, di(C₁ -C₃ alkyl)amino, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy,C₂ -C₅ alkylthioalkyl, C₂ -C₅ alkylsulfinylalkyl, C₂ -C₅alkylsulfonylalkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alkynyl, C₃ -C₅ cycloalkyl,azido, cyano, ##STR63## or N(OCH₃)CH₃ ; p is 2 or 3; Q³ and Q⁴ areindependently O or S; R¹⁴ is H or C₁ -C₃ alkyl; R¹⁵ and R¹⁶ areindependently C₁ -C₃ alkyl; and Z is CH, CCH₃, CC₂ H₅, CCl or CBr;andtheir agriculturally suitable salts; provided that 1) when X is halogen,then Z is CH and Y is OCH₃, OCH₂ CH₃, NH₂, NHCH₃, N(CH₃)₂, OCF₂ H, OCF₂Br or N(OCH₃)CH₃ ; and 2) when X or Y is C₁ haloalkoxy, then Z is CH. 2.The compounds of claim 1 whereX is C₁ -C₂ alkyl, C₁ -C₂ alkoxy, Cl, F,Br, I, OCF₂ H, CH₂ F, CF₃, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃, CH₂ Cl orCH₂ Br; Y is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, CH₂ OCH₃, CH₂ OCH₂ CH₃,NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂CH₂ OCH₃, CH₂ SCH₃, ##STR64## OCF₂ H, SCF₂ H, cyclopropyl, C.tbd.CH orC.tbd.CCH₃ ; R¹⁴ is H or CH₃ ; R¹⁵ and R¹⁶ are independently CH₃ or CH₂CH₃ ; Z is CH; and R is H.
 3. The compounds of claim 2 wherein L is L-1,L-2, L-3, L-7, L-8 or L-9.
 4. The compounds of claim 3 where R⁸ is H, C₁-C₃ alkyl or allyl.
 5. The compounds of claim 4 whereZ is CH; X is CH₃,OCH₃, OCH₂ CH₃, Cl or OCF₂ H; and Y is CH₃, OCH₃, CH(OCH₃)₂ or OCF₂ H.6. The compounds of claim 5 where L is L-1; and W is CH.
 7. Thecompounds of claim 5 where L is L-2.
 8. The compounds of claim 5 where Lis L-7.
 9. The compound of claim 1 which is3,4-dihydro-N-[[(4-methoxy-6-methyl-2-pyrimidin-2-yl)-amino]carbonyl]-1-oxo-1H-[1,4]-oxazine[4,3-a]indole-10-sulfonamide.10. The compound of claim 1 which isN-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3-4-dihydro-2H-pyrrolo[1,2-e]-[1,2,5]thiadiazine-8-sulfonamide,1,1-dioxide.
 11. The compound of claim 1 which isN-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-3,4-dihydro-2-methyl-2H-pyrazolo-[1,5-e][1,2,5]thiadiazine-8-sulfonamide,1,1,-dioxide.12. An agriculturally suitable composition for controlling the growth ofundesired vegetation comprising an effective amount of a compound ofclaim 1 and at least one of the following: surfactant, solid diluent orliquid diluent.
 13. An agriculturally suitable composition forcontrolling the growth of undesired vegetation comprising an effectiveamount of a compound of claim 2 and at least one of the following:surfactant, solid diluent or liquid diluent.
 14. An agriculturallysuitable composition for controlling the growth of undesired vegetationcomprising an effective amount of a compound of claim 3 and at least oneof the following: surfactant, solid diluent or liquid diluent.
 15. Anagriculturally suitable composition for controlling the growth ofundesired vegetation comprising an effective amount of a compound ofclaim 4 and at least one of the following: surfactant, solid diluent orliquid diluent.
 16. An agriculturally suitable composition forcontrolling the growth of undesired vegetation comprising an effectiveamount of a compound of claim 5 and at least one of the following:surfactant, solid diluent or liquid diluent.
 17. An agriculturallysuitable composition for controlling the growth of undesired vegetationcomprising an effective amount of a compound of claim 6 and at least oneof the following: surfactant, solid diluent or liquid diluent.
 18. Anagriculturally suitable composition for controlling the growth ofundesired vegetation comprising an effective amount of a compound ofclaim 7 and at least one of the following: surfactant, solid diluent orliquid diluent.
 19. An agriculturally suitable composition forcontrolling the growth of undesired vegetation comprising an effectiveamount of a compound of claim 8 and at least one of the following:surfactant, solid diluent or liquid diluent.
 20. An agriculturallysuitable composition for controlling the growth of undesired vegetationcomprising an effective amount of a compound of claim 9 and at least oneof the following: surfactant, solid diluent or liquid diluent.
 21. Anagriculturally suitable composition for controlling the growth ofundesired vegetation comprising an effective amount of a compound ofclaim 11 and at least one of the following: surfactant, solid diluent orliquid diluent.
 22. An agriculturally suitable composition forcontrolling the growth of undesired vegetation comprising an effectiveamount of a compound of claim 12 and at least one of the following:surfactant, solid diluent or liquid diluent.
 23. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound ofclaim
 1. 24. A method for controlling the growth of undesired vegetationwhich comprises applying to the locus to be protected an effectiveamount of a compound of claim
 2. 25. A method for controlling the growthof undesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 3. 26. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim4.
 27. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound in claim
 5. 28. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 6. 29. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim7.
 30. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 8. 31. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 9. 32. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim11.
 33. A method for controlling the growth of undesired vegetationwhich comprises applying to the locus to be protected an effectiveamount of a compound of claim 12.